METHOD FOR PREPARING BORIC ACID ESTER BASED ON LITHIUM COMPOUND

Abstract

A method for preparing the borate ester using a lithium compound includes: under the inert gas, stirring and mixing carboxylic acid and borane, and a catalyst lithium compound is added, then the borate ester is obtained with hydroboration; wherein the hydroboration is at room temperature for 10 to 80 min. After the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate esters with different substituents. The lithium compounds are n-butyl lithium, lithium aniline, p-methyl lithium aniline, o-methyl lithium aniline, 2-methoxyaniline lithium, 4-methoxyaniline lithium, 2,6-dimethylaniline lithium, and 2,6-diisopropylaniline lithium. The lithium compounds disclosed in the present invention can catalyze the boron hydrogenation reaction of carboxylic acid and borane with high activity under room temperature conditions; the amount of lithium compound is 0.1-0.9% of the molar amount of carboxylic acid.

Claims

1. A method for preparing a borate ester based using a lithium compound comprising the following steps: under inert gas, stirring and mixing a carboxylic acid and a borane, adding the lithium compound as a catalyst is added, and conducting a hydroboration to obtain the borate ester; wherein the lithium compound is n-butyllithium, anilinolithium, p-toluidine lithium, o-methylanilinide lithium, 2-methoxyanilinide lithium, 4-methoxy lithium anilinide, lithium 2,6,-dimethylanilinide, or lithium 2,6-diisopropylanilinide.

2. The method according to claim 1, wherein the borane is pinacolborane; and the carboxylic acid is acetic acid, caproic acid, valeric acid, heptanoic acid, trimethyl acetic acid, adipic acid, benzoic acid, 4-bromobenzoic acid, 4-fluorobenzoic acid, 1-naphthoic acid, 2-methoxybenzoic acid, o-carboxyphenylacetic acid, 3-indole acetic acid, 2-phenylbutyl Acid, 2-methyl-5-bromo-benzoic acid, 4-tert-butylbenzoic acid, 2-bromobenzoic acid, 4-iodobenzoic acid, 3-phenylpropionic acid, or diphenylacetic acid.

3. The method according to claim 1, wherein a molar ratio of the carboxylic acid to the borane is 1:3 to 1:7; and an amount of the lithium compound is 0.1% to 0.9% of a molar amount of the carboxylic acid.

4. The method according to claim 1, wherein the hydroboration is conducted at room temperature for 10 to 80 min.

5. The method according to claim 1, wherein the hydroboration is stopped by contacting air, a solvent is removed under reduced pressure to obtain the borate ester.

6. A method for preparing an alcohol compound using on lithium compound, comprising the following steps: under inert gas, stirring and mixing a carboxylic acid and a borane, adding the lithium compound as a catalyst, and conducting a hydroboration to obtain the borate ester; after the hydroboration, adding silica gel and methanol, conducting a hydrolysis reaction to obtain the alcohol compound, wherein the lithium compound is n-butyllithium, aniline lithium, p-toluidine lithium, o-methylanilinide lithium, 2-methoxyanilinide lithium, 4-methoxy lithium anilinide, lithium 2,6,-dimethylanilinide, or lithium 2,6-diisopropylanilinide.

7. The method according to claim 6, wherein the hydroboration is stopped by contacting air, a solvent is removed under reduced pressure; silica gel and methanol are added; after the hydrolysis reaction, a solvent is removed under reduced pressure, and the alcohol compound is obtained by column chromatography.

8. The method according to claim 6, wherein a ratio of carboxylic acid and silica gel, and methanol is 1 mmol:2 to 2.2 g:6 mL; a molar ratio of the carboxylic acid to borane is 1:3 to 1:7; and an amount of the lithium compound is 0.1% to 0.9% of a molar amount of the carboxylic acid.

9. The method according to claim 6, wherein hydrolysis reaction is conducted at 50° C. for 115 to 120 min; the hydroboration is conducted at room temperature for 10 to 80 min.

10. The method according to claim 6, wherein the borane is pinacolborane; and the carboxylic acid is acetic acid, caproic acid, valeric acid, heptanoic acid, trimethyl acetic acid, adipic acid, benzoic acid, 4-bromobenzoic acid, 4-fluorobenzoic acid, 1-naphthoic acid, 2-methoxybenzoic acid, o-carboxyphenylacetic acid, 3-indole acetic acid, 2-phenylbutyl acid, 4-iodobenzoic acid, 3-phenylpropionic acid, diphenylacetic acid, 2-phenylbutyric acid, indole-3-acetic acid, o-carboxyphenylacetic acid, or 2-methyl-5-bromobenzoic acid.

Description

DESCRIPTION OF THE DRAWINGS

[0025] FIG. 1 is the schematic diagram of the reaction in Example 1;

[0026] FIG. 2 is chemical structural formula of the 2,4-bis(2,6-diisopropylanilino)-2-pentenyllithium in comparative example.

EMBODIMENTS OF THE INVENTION

[0027] The present invention will be further described in combination with the following embodiments:

Example 1

[0028] The schematic diagram of the reaction is shown in FIG. 1, and the reaction process in other embodiments is similar to this.

[0029] Under the protection of inert gas, loading the benzoic acid (61.1 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (218 μL, 1.5 mmol) with pipette gun, and finally adding 25 μL of tetrahydrofuran solution of n-butyl lithium (0.1M) (0.5 mol %, the same below), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.15 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 97%, .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.22-7.32 (m, 5H, ArH), 4.92 (s, 2H, CH.sub.2), 1.26 (s, 36H, CH.sub.3); when the amount of the pinacolborane is 2 mmol, conversion rate of .sup.1H is 99%; when the amount of the pinacolborane is 361.2 μL, 2.5 mmol, conversion rate of .sup.1H is 99%. If with the triaryloxy rare earth catalyst Nd(OAr).sub.3(THF).sub.2, no product can be obtained instead.

[0030] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 93%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.21-7.29 (m, 5H, ArH), 4.62 (s, 2H, CH.sub.2), 1.87 (br s, 1H, OH).

Comparative Example: The Hydroboration of Benzoic Acid and Pinacol Borane Catalyzed by 2,4-bis(2,6-diisopropylanilino)-2-pentenyllithium

[0031] Under the protection of inert gas, loading the benzoic acid (60.5 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (238 μL, 1.65 mmol) with pipette gun, and finally adding 25 μL of tetrahydrofuran solution of 2,4-bis(2,6-diisopropylanilino)-2-pentenyllithium (0.1M) (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.32 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 12%, .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.22-7.32 (m, 5H, ArH), 4.92 (s, 2H, CH.sub.2), 1.26 (s, 36H, CH.sub.3). If the raw material is replaced with acetic acid (28.6 μL, 0.5 mmol) conversion rate of .sup.1H is 18%; .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 3.87 (q, 2H, CH.sub.2), 1.24 (s, 36H, CH.sub.3), 1.20 (br s, 3H, CH.sub.3).

[0032] The chemical structural formula of the 2,4-bis(2,6-diisopropylanilino)-2-pentenyllithium in comparative example is shown in FIG. 2.

Example 2

[0033] Under the protection of inert gas, loading the benzoic acid (61.1 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (218 μL, 1.5 mmol) with pipette gun, and finally adding 40 μL of tetrahydrofuran solution of aniline lithium (0.1M) (0.8 mol %, the same below), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.15 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. If with the triaryloxy rare earth catalyst Nd(OAr).sub.3(THF).sub.2, no product can be obtained instead. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.20-7.30 (m, 5H, ArH), 4.91 (s, 2H, CH.sub.2), 1.24 (s, 36H, CH.sub.3); when the amount of the pinacolborane is 2 mmol, conversion rate of .sup.1H is 99%; when the amount of the pinacolborane is 361.2 μL, 2.5 mmol, conversion rate of .sup.1H is 99%.

[0034] The reaction is carried out at room temperature for 80 minutes, the yield is 99%.

Example 3

[0035] Under the protection of inert gas, loading the 4-fluorobenzoic acid (70.8 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.99 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 91%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.20-7.30 (m, 5H, ArH), 4.91 (s, 2H, CH.sub.2), 1.24 (s, 36H, CH.sub.3).

Example 4

[0036] Under the protection of inert gas, loading the 4-bromobenzoic acid (100 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (289 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of o-methylanilinide lithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.67 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 93%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.39 (br s, 2H, ArCH), 7.16 (t, 2H, ArCH), 4.80 (s, 2H, OCH.sub.2), 1.19 (s, 36H, CH.sub.3).

Example 5

[0037] Under the protection of inert gas, loading the 4-fluorobenzoic acid (70.8 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.99 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 90%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.21 (br s, 2H, ArCH), 6.91 (t, 2H, ArCH), 4.75 (s, 2H, OCH.sub.2), 1.15 (s, 36H, CH.sub.3).

[0038] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol are extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 89%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.22 (br s, 2H, ArCH), 6.98 (t, 2H, ArCH), 4.56 (s, 2H, CH.sub.2), 2.27 (br s, 1H, OH).

Example 6

[0039] Under the protection of inert gas, loading the 4-bromobenzoic acid (100 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (289 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.67 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 95%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.40 (br s, 2H, ArCH), 7.17 (t, 2H, ArCH), 4.81 (s, 2H, OCH.sub.2), 1.20 (s, 36H, CH.sub.3).

[0040] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 91%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.42 (br s, 2H, ArCH), 7.19 (t, 2H, ArCH), 4.60 (s, 2H, CH.sub.2), 2.26 (br s, 1H, OH).

Example 7

[0041] Under the protection of inert gas, loading the 2-methoxybenzoic acid (76.2 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.23 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.41 (d, 1H, ArCH), 7.21 (t, 1H, ArCH), 6.95 (t, 1H, ArCH), 6.83 (d, 1H, ArCH), 4.97 (s, 2H, OCH.sub.2), 1.26 (s, 36H, CH.sub.3).

[0042] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 91%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.42 (d, 1H, ArCH), 7.23 (t, 1H, ArCH), 6.96 (t, 1H, ArCH), 6.84 (d, 1H, ArCH), 4.67 (s, 2H, CH.sub.2), 3.87 (br s, 1H, OH), 1.23 (s, 3H, CH.sub.3).

Example 8

[0043] Under the protection of inert gas, loading the 1-naphthoic acid (85.4 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.42 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 91%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 8.01 (d, 1H, ArCH), 7.78-7.81 (m, 2H, ArCH), 7.74 (d, 1H, ArCH), 7.37-7.47 (m, 3H, ArCH), 5.36 (s, 2H, OCH.sub.2), 1.22 (s, 36H, CH.sub.3).

[0044] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 90%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 8.02 (d, 1H, ArCH), 7.80-7.82 (m, 2H, ArCH), 7.73 (d, 1H, ArCH), 7.38-7.48 (m, 3H, ArCH), 5.01 (s, 2H, CH.sub.2), 2.31 (br s, 1H, OH).

Example 9

[0045] Under the protection of inert gas, loading the 4-tert-butyl benzoic (88.9 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.89 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.27 (d, 2H, ArCH), 7.18 (d, 2H, ArCH), 4.81 (s, 2H, OCH.sub.2), 1.22 (s, 9H, CH3, tBu), 1.17 (s, 36H, CH.sub.3).

[0046] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 93%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.28 (d, 2H, ArCH), 7.16 (d, 2H, ArCH), 4.51 (s, 2H, CH.sub.2), 2.12 (br s, 1H, OH), 1.23 (s, 9H, CH.sub.3, tBu).

Example 10

[0047] Under the protection of inert gas, loading the 2-bromobenzoic acid (100.6 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.17 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.40 (d, 2H, ArCH), 7.18-7.21 (m, 1H, ArCH), 7.02 (t, 1H, ArCH), 4.89 (s, 2H, OCH.sub.2), 1.18 (s, 36H, CH.sub.3).

[0048] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 91%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.41 (d, 2H, ArCH), 7.19-7.22 (m, 1H, ArCH), 7.03 (t, 1H, ArCH), 4.71 (s, 2H, CH.sub.2), 2.41 (br s, 1H, OH).

Example 11

[0049] Under the protection of inert gas, loading the 4-iodobenzoic acid (124.0 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.09 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.56 (d, 2H, ArCH), 7.01 (d, 2H, ArCH), 4.77 (s, 2H, OCH.sub.2), 1.17 (s, 36H, CH.sub.3).

[0050] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 91%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.57 (d, 2H, ArCH), 7.02 (d, 2H, ArCH), 4.65 (s, 2H, CH.sub.2), 2.15 (br s, 1H, OH).

Example 12

[0051] Under the protection of inert gas, loading the 3-phenylpropionic acid (74.9 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (289 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.89 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.17 (t, 2H, ArCH), 7.04-7.09 (m, 3H, ArCH), 3.79 (t, 2H, CH.sub.2, OCH.sub.2), 2.61 (t, 2H, CH.sub.2), 1.75-1.82 (m, 2H, CH.sub.2), 1.16 (s, 36H, CH.sub.3).

[0052] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 95%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.23 (t, 2H, ArCH), 7.11-7.13 (m, 3H, ArCH), 3.62 (t, 2H, CH.sub.2, OCH.sub.2), 2.65 (t, 2H, CH.sub.2), 1.78-1.85 (m, 2H, CH.sub.2), 1.61 (br s, 1H, OH).

Example 13

[0053] Under the protection of inert gas, loading the diphenylacetic acid (105.8 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (289 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.84 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.13-7.32 (m, 10H, ArCH), 4.41 (d, 2H, CH.sub.2, OCH.sub.2), 4.24 (t, 1H, CH), 1.23 (s, 24H, CH.sub.3, pinBOBpin), 1.12 (s, 12H, CH.sub.3, OBpin).

[0054] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 91%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.20-7.31 (m, 10H, ArCH), 4.19 (t, 1H, CH), 4.13 (d, 2H, CH.sub.2), 1.64-1.70 (t, 1H, OH).

Example 14

[0055] Under the protection of inert gas, loading the 2-methyl-5-bromobenzoic acid (107.1 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (289 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.77 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 6.90 (d, 1H, ArCH), 7.19 (d, 1H, ArCH), 7.47 (s, 1H, ArCH), 4.77 (s, 2H, OCH.sub.2), 2.12 (s, 3H, CH.sub.3), 1.17 (s, 36H, CH.sub.3).

[0056] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 95%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 6.91 (d, 1H, ArCH), 7.22 (d, 1H, ArCH), 7.57 (s, 1H, ArCH), 4.44 (s, 2H, OCH.sub.2), 2.15 (s, 3H, CH.sub.3), 2.25 (br s, 1H, OH).

Example 15

[0057] Under the protection of inert gas, loading the 2-phenylbutyric acid (82.2 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.20 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.15-7.19 (m, 2H, ArCH), 7.08-7.10 (m, 3H, ArCH), 3.83-3.93 (m, 2H, CH.sub.2, OCH.sub.2), 2.57-2.66 (m, 1H, CH), 1.70-1.79 (m, 1H, CH.sub.2), 1.46-1.55 (m, 1H, CH.sub.2), 1.16 (s, 36H, CH.sub.3, OBpin & pinBOBpin), 0.74 (t, 3H, CH.sub.3).

[0058] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 93%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.17-7.30 (m, 5H, ArCH), 3.66-3.68 (m, 2H, CH.sub.2, OCH.sub.2), 2.64 (m, 1H, CH), 1.54-1.73 (m, 1H, CH.sub.2), 1.87 (s, 1H, OH), 0.82 (t, 3H, CH.sub.3).

Example 16

[0059] Under the protection of inert gas, loading the 3-indole acetic acid (88.0 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (363 μL, 2.5 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.49 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 95%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.82 (d, 1H, ArCH), 7.45 (d, 1H, ArCH), 7.02-7.15 (m, 3H, ArCH), 4.06 (t, 2H, OCH.sub.2), 2.90 (t, 2H, CH.sub.2), 1.29 (s, 12H, CH.sub.3, N-Bpin) 1.14 (s, 24H, CH.sub.3, pinBOBpin), 1.06 (s, 12H, CH.sub.3, OBpin).

[0060] Adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 91%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 8.10 (s, 1H, NH), 7.83 (d, 1H, ArCH), 7.45 (d, 1H, ArCH), 7.03-7.15 (m, 3H, ArCH), 4.67 (t, 2H, OCH.sub.2), 3.28 (t, 2H, CH.sub.2), 1.90 (br s, 1H, OH).

Example 17

[0061] Under the protection of inert gas, loading the o-carboxyphenylacetic acid (90.0 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (508 μL, 3.5 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.02 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.33 (br s, 1H, ArCH), 7.11 (br s, 3H, ArCH), 4.90 (s, 2H, CH.sub.2). 3.96 (t, 2H, CH.sub.2), 2.86 (t, 2H, CH.sub.2), 1.17 (s, 72H, CH.sub.3, OBpin & pinBOBpin). Continuing hydrolyzing to obtain pure primary alcohol, adding 1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 93%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.32 (br s, 1H, ArCH), 7.12 (br s, 3H, ArCH), 4.53 (s, 2H, CH.sub.2), 3.76 (t, 2H, CH.sub.2OH), 3.7 (br, 1H, OH), 3.1 (br s, 1H, OH), 2.86 (t, 2H, CH.sub.2).

Example 18

[0062] Under the protection of inert gas, loading the 2-methoxybenzoic acid (76.2 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.23 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.40 (d, 1H, ArCH), 7.21 (t, 1H, ArCH), 6.94 (t, 1H, ArCH), 6.82 (d, 1H, ArCH), 4.96 (s, 2H, OCH.sub.2), 1.25 (s, 36H, CH.sub.3).

Example 19

[0063] Under the protection of inert gas, loading the 1-naphthoic acid (85.4 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (289 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.42 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 93%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 8.01 (d, 1H, ArCH), 7.78-7.80 (m, 2H, ArCH), 7.73 (d, 1H, ArCH), 7.36-7.46 (m, 3H, ArCH), 5.35 (s, 2H, OCH.sub.2), 1.21 (s, 36H, CH.sub.3).

Example 20

[0064] Under the protection of inert gas, loading the 4-tert-butyl benzoic acid (88.9 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of 2-methoxyanilinide lithium (0.8 mol %), at room temperature for 80 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.89 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.25 (d, 2H, ArCH), 7.16 (d, 2H, ArCH), 4.79 (s, 2H, OCH.sub.2), 1.20 (s, 9H, CH.sub.3, tBu), 1.15 (s, 36H, CH.sub.3).

Example 21

[0065] Under the protection of inert gas, loading the 2-bromobenzoic acid (100.6 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.17 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.39 (d, 2H, ArCH), 7.17-7.20 (m, 1H, ArCH), 7.01 (t, 1H, ArCH), 4.88 (s, 2H, OCH.sub.2), 1.17 (s, 36H, CH.sub.3).

Example 22

[0066] Under the protection of inert gas, loading the 4-iodobenzoic acid (124.0 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of 4-lithium methoxyanilide (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.09 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.55 (d, 2H, ArCH), 7.01 (d, 2H, ArCH), 4.76 (s, 2H, OCH.sub.2), 1.16 (s, 36H, CH.sub.3).

Example 23

[0067] Under the protection of inert gas, loading the 3-phenylpropionic acid (74.9 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (289 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.89 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.16 (t, 2H, ArCH), 7.03-7.08 (m, 3H, ArCH), 3.78 (t, 2H, CH.sub.2, OCH.sub.2), 2.60 (t, 2H, CH.sub.2), 1.74-1.81 (m, 2H, CH.sub.2), 1.15 (s, 36H, CH.sub.3).

Example 24

[0068] Under the protection of inert gas, loading the diphenylacetic acid (105.8 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (289 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.84 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.12-7.31 (m, 10H, ArCH), 4.40 (d, 2H, CH.sub.2, OCH.sub.2), 4.23 (t, 1H, CH), 1.22 (s, 24H, CH.sub.3, pinBOBpin), 1.11 (s, 12H, CH.sub.3, OBpin).

Example 25

[0069] Under the protection of inert gas, loading the 2-methyl-5-bromo-benzoic acid (107.1 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (289 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.77 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 6.91 (d, 1H, ArCH), 7.20 (d, 1H, ArCH), 7.48 (s, 1H, ArCH), 4.78 (s, 2H, OCH2), 2.13 (s, 3H, CH3), 1.18 (s, 36H, CH3).

Example 26

[0070] Under the protection of inert gas, loading the 2-phenylbutyric acid (82.2 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.20 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.14-7.18 (m, 2H, ArCH), 7.07-7.10 (m, 3H, ArCH), 3.82-3.92 (m, 2H, CH2, OCH2), 2.56-2.65 (m, 1H, CH), 1.70-1.80 (m, 1H, CH2), 1.45-1.54 (m, 1H, CH2), 1.15 (s, 36H, CH3, OBpin & pinBOBpin), 0.73 (t, 3H, CH3).

Example 27

[0071] Under the protection of inert gas, loading the 3-indole acetic acid (88.0 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (363 μL, 2.5 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.49 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 96%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.81 (d, 1H, ArCH), 7.44 (d, 1H, ArCH), 7.01-7.13 (m, 3H, ArCH), 4.05 (t, 2H, OCH.sub.2), 2.89 (t, 2H, CH.sub.2), 1.28 (s, 12H, CH.sub.3, N-Bpin) 1.13 (s, 24H, CH.sub.3, pinBOBpin), 1.05 (s, 12H, CH.sub.3, OBpin).

Example 28

[0072] Under the protection of inert gas, loading the o-carboxyphenylacetic acid (90.0 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (508 μL, 3.5 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.02 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.32 (br s, 1H, ArCH), 7.10 (br s, 3H, ArCH), 4.89 (s, 2H, CH.sub.2), 3.95 (t, 2H, CH.sub.2), 2.85 (t, 2H, CH.sub.2), 1.16 (s, 72H, CH.sub.3, OBpin & pinBOBpin).

Example 29

[0073] Under the protection of inert gas, loading the benzoic acid (61.1 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (218 μL, 1.5 mmol) with pipette gun, and finally adding 40 μL of tetrahydrofuran solution of lithium p-tolylamine (0.1M) (0.8 mol %), at room temperature for 70 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.15 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.23-7.33 (m, 5H, ArH), 4.93 (s, 2H, CH.sub.2), 1.27 (s, 36H, CH.sub.3).

Example 30

[0074] Under the protection of inert gas, loading the 3-indole acetic acid (88.0 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (363 μL, 2.5 mmol) with pipette gun, and finally adding tetrahydrofuran solution of 2,6-dimethylanilinolithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.49 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 96%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.86 (d, 1H, ArCH), 7.49 (d, 1H, ArCH), 7.06-7.18 (m, 3H, ArCH), 4.10 (t, 2H, OCH.sub.2), 2.94 (t, 2H, CH.sub.2), 1.33 (s, 12H, CH.sub.3, N-Bpin) 1.18 (s, 24H, CH.sub.3, pinBOBpin), 1.10 (s, 12H, CH.sub.3, OBpin).

Example 31

[0075] Under the protection of inert gas, loading the 2-phenylbutyric acid (82.2 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of 2,6-diisopropylanilinolithium (0.1M) (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.20 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.20-7.24 (m, 2H, ArCH), 7.13-7.15 (m, 3H, ArCH), 3.88-3.98 (m, 2H, CH.sub.2, OCH.sub.2), 2.62-2.71 (m, 1H, CH), 1.75-1.84 (m, 1H, CH.sub.2), 1.51-1.60 (m, 1H, CH.sub.2), 1.21 (s, 36H, CH.sub.3, OBpin & pinBOBpin), 0.79 (t, 3H, CH.sub.3).

Example 32

[0076] Under the protection of inert gas, loading the 2-methyl-5-bromobenzoic acid (107.1 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (289 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of p-toluidine lithium (0.8 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.77 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 6.92 (d, 1H, ArCH), 7.21 (d, 1H, ArCH), 7.49 (s, 1H, ArCH), 4.79 (s, 2H, OCH.sub.2), 2.14 (s, 3H, CH.sub.3), 1.19 (s, 36H, CH.sub.3).

Example 33

[0077] Under the protection of inert gas, loading the o-carboxyphenylacetic acid (90.0 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (508 μL, 3.5 mmol) with pipette gun, and finally adding tetrahydrofuran solution of lithium anilinolide (0.8 mol %), at room temperature for 80 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.02 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 7.36 (br s, 1H, ArCH), 7.14 (br s, 3H, ArCH), 4.93 (s, 2H, CH.sub.2), 3.99 (t, 2H, CH.sub.2), 2.89 (t, 2H, CH.sub.2), 1.20 (s, 72H, CH.sub.3, OBpin & pinBOBpin).

Example 34

[0078] Under the protection of inert gas, loading the 1-naphthoic acid (85.4 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (289 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of lithium 2,6,-dimethylanilinide (0.7 mol %), at room temperature for 75 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.42 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 93%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 8.05 (d, 1H, ArCH), 7.83-7.85 (m, 2H, ArCH), 7.78 (d, 1H, ArCH), 7.38-7.48 (m, 3H, ArCH), 5.37 (s, 2H, OCH.sub.2), 1.26 (s, 36H, CH.sub.3).

Example 35

[0079] Under the protection of inert gas, loading the acetic acid (28.6 μL, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding 10 μL tetrahydrofuran solution of n-butyl lithium (0.1M) (0.2 mol %), at room temperature for 15 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.08 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. If the n-butyllithium is replaced with 2,4-bis(2,6-diisopropylanilino)-2-pentenyllithium, conversion rate of .sup.1H is 15%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 3.88 (q, 2H, CH.sub.2), 1.25 (s, 36H, CH.sub.3), 1.21 (br s, 3H, CH.sub.3).

[0080] Adding 1.1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 115 min. After the reaction the product aliphatic alcohol compounds are extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 95%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.69 (q, 2H, CH.sub.2), 2.92 (br s, 1H, OH), 1.22 (br s, 3H, CH.sub.3).

[0081] When pinacol borane (218 μL, 1.5 mmol), the yield of borate is 95%; when pinacol borane (363 μL, 2.5 mmol), the yield of borate is 99%; reaction time is 20 min, The borate yield is 99%; if the n-butyl lithium is replaced with the triaryloxy rare earth catalyst, Nd(OAr).sub.3(THF).sub.2, the product borate cannot be obtained.

Example 36

[0082] Under the protection of inert gas, loading the valeric acid (54.38 μL, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.2 mol %), at room temperature for 15 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.12 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 92%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 3.81 (t, 2H, OCH.sub.2), 1.52-1.56 (m, 2H, CH.sub.2), 1.30-1.52 (m, 4H, CH.sub.2), 1.28 (s, 36H, CH), 0.86 (t, 3H, CH.sub.3).

[0083] Adding 1.1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 115 min. After the reaction the product aliphatic alcohol compounds are extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 92%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.63 (t, 2H, OCH.sub.2), 1.59 (m, 2H, CH.sub.2), 1.35 (m, 2H, CH.sub.2), 2.35 (br s, 1H, OH), 0.90 (t, 3H, CH.sub.3).

Example 37

[0084] Under the protection of inert gas, loading the caproic acid (62.52 μL, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.2 mol %), at room temperature for 15 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.01 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 90%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.76 (t, 2H, OCH.sub.2), 1.46-1.52 (m, 2H, CH.sub.2), 1.24-1.35 (m, 6H, CH.sub.2), 1.19 (s, 48H, CH.sub.3), 0.82 (t, 3H, CH.sub.3).

[0085] Adding 1.1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 115 min. After the reaction the product aliphatic alcohol compounds are extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 89%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.75 (t, 2H, OCH.sub.2), 1.47-1.52 (m, 2H, CH.sub.2), 1.26-1.36 (m, 6H, CH.sub.2), 1.71 (br s, 1H, OH.sub.3), 0.82 (t, 3H, CH.sub.3).

Example 38

[0086] Under the protection of inert gas, loading the heptanoic acid (70.90 μL, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.2 mol %), at room temperature for 15 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.05 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 90%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.71 (t, 2H, OCH.sub.2), 1.41-1.47 (m, 2H, CH.sub.2), 1.19-1.30 (m, 8H, CH.sub.2), 1.24 (s, 48H, CH.sub.3), 0.77 (t, 3H, CH.sub.3).

[0087] Adding 1.1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 115 min. After the reaction the product aliphatic alcohol compounds are extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 88%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.72 (t, 2H, OCH.sub.2), 1.42-1.47 (m, 2H, CH.sub.2), 1.20-1.30 (m, 8H, CH.sub.2), 1.76 (br s, 1H, OH.sub.3), 0.77 (t, 3H, CH.sub.3).

Example 39

[0088] Under the protection of inert gas, loading the trimethylacetic acid (50.7 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (288 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.2 mol %), at room temperature for 15 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.08 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.43 (s, 2H, OCH.sub.2), 1.17 (s, 36H, CH.sub.3, OBpin & pinBOBpin), 0.82 (s, 9H, CH.sub.3).

[0089] Adding 1.1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 115 min. After the reaction the product aliphatic alcohol compounds are extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 92%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.20 (s, 2H, OCH.sub.2), 1.97 (br s, 1H, OH), 0.81 (s, 9H, CH.sub.3).

Example 40

[0090] Under the protection of inert gas, loading the adipic acid (72.9 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (508 μL, 3.5 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.2 mol %), at room temperature for 15 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.90 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.77 (t, 4H, OCH.sub.2), 1.48-1.50 (m, 4H, CH.sub.2), 1.28-1.30 (m, 4H, CH.sub.2), 1.17 (s, 72H, CH.sub.3, OBpin & pinBOBpin).

[0091] Adding 1.1 g of silica gel and 3 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 115 min. After the reaction the product aliphatic alcohol compounds are extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 92%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 3.76 (t, 4H, OCH.sub.2), 1.48-1.50 (m, 4H, CH.sub.2), 1.29-1.31 (m, 4H, CH.sub.2), 2.25 (br s, 2H, OH).

Example 41

[0092] Under the protection of inert gas, loading the acetic acid (28.6 μL, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding 30 μL tetrahydrofuran solution of aniline lithium (0.1M) (0.6 mol %, the same below), at room temperature for 55 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.08 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 3.86 (q, 2H, CH.sub.2), 1.24 (s, 36H, CH.sub.3), 1.20 (br s, 3H, CH.sub.3).

[0093] When pinacol borane (218 μL, 1.5 mmol), the yield of borate is 96%; when pinacol borane (363 μL, 2.5 mmol), the yield of borate is 99%; reaction time is 30 min, The borate yield is 99%; if the n-butyl lithium is replaced with the triaryloxy rare earth catalyst, Nd(OAr).sub.3(THF).sub.2, the product borate cannot be obtained. If anilinolithium is replaced with p-toluidine lithium, o-toluidine lithium, 2-methoxy lithium anilide, lithium 4-methoxyanilide, lithium 2,6,-dimethylanilide or lithium 2,6-diisopropylanilide, the conversion rates of .sup.1H are all 99%.

Example 42

[0094] Under the protection of inert gas, loading the valeric acid (54.38 μL, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.6 mol %), at room temperature for 55 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.12 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 92%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl.sub.3): δ 3.80 (t, 2H, OCH.sub.2), 1.51-1.55 (m, 2H, CH.sub.2), 1.29-1.51 (m, 4H, CH.sub.2), 1.27 (s, 36H, CH), 0.85 (t, 3H, CH.sub.3).

Example 43

[0095] Under the protection of inert gas, loading the hexanoic acid (62.52 μL, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding 30 μL tetrahydrofuran solution of aniline lithium (0.6 mol %), at room temperature for 55 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.01 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 90%.

[0096] If anilinolithium is replaced with p-toluidine lithium, o-toluidine lithium, 2-methoxy Lithium anilide, lithium 4-methoxyanilide, lithium 2,6,-dimethylanilide or lithium 2,6-diisopropylanilide, the conversion rates of .sup.1H is 91%, 90%, 93%, 90%, 91%, 92%.

[0097] .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.75 (t, 2H, OCH.sub.2), 1.45-1.51 (m, 2H, CH.sub.2), 1.23-1.34 (m, 6H, CH.sub.2), 1.18 (s, 48H, CH.sub.3), 0.81 (t, 3H, CH.sub.3).

Example 44

[0098] Under the protection of inert gas, loading the heptanoic acid (70.90 μL, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (290 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.6 mol %), at room temperature for 55 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.05 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 90%. .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.70 (t, 2H, OCH.sub.2), 1.40-1.46 (m, 2H, CH.sub.2), 1.18-1.29 (m, 8H, CH.sub.2), 1.23 (s, 48H, CH.sub.3), 0.76 (t, 3H, CH.sub.3).

Example 45

[0099] Under the protection of inert gas, loading the trimethylacetic acid (50.7 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (289 μL, 2 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.6 mol %), at room temperature for 55 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.08 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. If anilinolithium is replaced with p-toluidine lithium, o-toluidine lithium, 2-methoxy lithium anilide, lithium 4-methoxyanilide, lithium 2,6,-dimethylanilide or lithium 2,6-diisopropylanilide, the conversion rates of .sup.1H is 96%, 99%, 98%, 99%, 99%, 97%.

[0100] .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.42 (s, 2H, OCH.sub.2), 1.16 (s, 36H, CH.sub.3, OBpin & pinBOBpin), 0.81 (s, 9H, CH.sub.3).

Example 46

[0101] Under the protection of inert gas, loading the adipic acid (72.9 mg, 0.5 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (508 μL, 3.5 mmol) with pipette gun, and finally adding tetrahydrofuran solution of aniline lithium (0.6 mol %), at room temperature for 55 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (83.90 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%. If anilinolithium is replaced with p-toluidine lithium, o-toluidine lithium, 2-methoxy lithium anilide, lithium 4-methoxyanilide, lithium 2,6,-dimethylanilide or lithium 2,6-diisopropylanilide, the conversion rates of .sup.1H is 99%, 99%, 98%, 99%, 97%, 96%.

[0102] .sup.1H NMR analysis of the product borate ester is: .sup.1H NMR (400 MHz, CDCl3): δ 3.76 (t, 4H, OCH.sub.2), 1.47-1.49 (m, 4H, CH.sub.2), 1.27-1.29 (m, 4H, CH.sub.2), 1.16 (s, 72H, CH.sub.3, OBpin & pinBOBpin).

Example 47

[0103] Under the protection of inert gas, loading the benzoic acid (50 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (200 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.1M) (0.5 mol %), at room temperature for 45 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.15 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%.

[0104] Adding 100 g of silica gel and 300 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 2 h. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 94%.

Example 48

[0105] Under the protection of inert gas, loading the acetic acid (50 mmol) to the reaction bottle, which is treated by dehydration and deoxidation, then adding a pinacolborane (200 mmol) with pipette gun, and finally adding tetrahydrofuran solution of n-butyl lithium (0.1M) (0.2 mol %), at room temperature for 15 min, then the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate ester. The mes-trimethoxybenzene (84.08 mg, 0.5 mmol) is used as the internal standard. The stock solution is dissolved in CDCl.sub.3 stirring for 10 minutes, sampled, and equipped with nuclear magnetism. After calculation, conversion rate of .sup.1H is 99%.

[0106] Adding 110 g of silica gel and 300 mL of methanol to the system where the solvent is removed after the hydroboration, and react at 50° C. for 115 min. After the reaction the product pure primary alcohol is extracted three times with ethyl acetate, and the organic layers were combined, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and purified by silica gel (100-200 mesh) column chromatography, washed with ethyl acetate/hexane (1:5 volume ratio) mixture, with a separation yield of 95%.