Method of making a second olefin using a first olefin, comprising steps (A) and (B): (A) performing a metathesis reaction with the first olefin in the presence of a metal complex configured to catalyse said metathesis reaction; (B) epoxidizing an olefin contained in the reaction mixture obtained in step (A) to form an epoxide; and deoxygenizing said epoxide to form said second olefin.

The present invention relates to a novel and improved process for preparing (3S)-3-(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)-3-cyclopropylpropanoic acid of the formula (I), to the compound of the formula (I) in crystalline form and to their use for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of cardiovascular, cardiopulmonary and cardiorenal disorders.

The present invention relates to a novel and improved process for preparing (3S)-3-(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)-3-cyclopropylpropanoic acid of the formula (I), to the compound of the formula (I) in crystalline form and to their use for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of cardiovascular, cardiopulmonary and cardiorenal disorders.

A process for preparing methyl methacrylate by direct oxidative esterification of methacrolein has elevated yields compared to known processes. Methyl methacrylate (MMA) is used in large amounts for preparing polymers and copolymers with other polymerizable compounds. In addition, methyl methacrylate is an important synthesis unit for a variety of specialty esters based on methacrylic acid (MAA), which can be produced by transesterification with the appropriate alcohol. There is consequently a great interest in very simple, economic, and environmentally friendly processes for preparing methyl methacrylate. A superior workup of the reactor output from the oxidative esterification of methacrolein allows specific by-products to be isolated and then additionally converted to alkyl methacrylates, especially to MMA.

A process for preparing methyl methacrylate by direct oxidative esterification of methacrolein has elevated yields compared to known processes. Methyl methacrylate (MMA) is used in large amounts for preparing polymers and copolymers with other polymerizable compounds. In addition, methyl methacrylate is an important synthesis unit for a variety of specialty esters based on methacrylic acid (MAA), which can be produced by transesterification with the appropriate alcohol. There is consequently a great interest in very simple, economic, and environmentally friendly processes for preparing methyl methacrylate. A superior workup of the reactor output from the oxidative esterification of methacrolein allows specific by-products to be isolated and then additionally converted to alkyl methacrylates, especially to MMA.

A process for preparing methyl methacrylate by direct oxidative esterification of methacrolein has elevated yields compared to known processes. Methyl methacrylate (MMA) is used in large amounts for preparing polymers and copolymers with other polymerizable compounds. In addition, methyl methacrylate is an important synthesis unit for a variety of specialty esters based on methacrylic acid (MAA), which can be produced by transesterification with the appropriate alcohol. There is consequently a great interest in very simple, economic, and environmentally friendly processes for preparing methyl methacrylate. A superior workup of the reactor output from the oxidative esterification of methacrolein allows specific by-products to be isolated and then additionally converted to alkyl methacrylates, especially to MMA.

Described herein is a process for the preparation of a mixture of compounds of formula

##STR00001##

having a weight ratio of the cis-diastereomers to trans-diastereoisomers higher than 1:1, where R.sub.1 represents a C.sub.1-8 alkyl group, a C.sub.2-8 alkenyl group or a C.sub.2-8 alkynyl group, each optionally substituted with one or two of a C.sub.1-4 alkyl alkoxy ether group and/or a C.sub.1-4 alkyl carboxylester group and R.sub.2 represents a C.sub.1-6 alkyl, a C.sub.2-6 alkenyl or a C.sub.2-6 alkynyl group, each optionally substituted with a C.sub.1-4 alkyl alkoxy ether group, a carboxylic acid group or a C.sub.1-4 alkyl carboxylester group and compounds suitable in the process.

Described herein is a process for the preparation of a mixture of compounds of formula

##STR00001##

having a weight ratio of the cis-diastereomers to trans-diastereoisomers higher than 1:1, where R.sub.1 represents a C.sub.1-8 alkyl group, a C.sub.2-8 alkenyl group or a C.sub.2-8 alkynyl group, each optionally substituted with one or two of a C.sub.1-4 alkyl alkoxy ether group and/or a C.sub.1-4 alkyl carboxylester group and R.sub.2 represents a C.sub.1-6 alkyl, a C.sub.2-6 alkenyl or a C.sub.2-6 alkynyl group, each optionally substituted with a C.sub.1-4 alkyl alkoxy ether group, a carboxylic acid group or a C.sub.1-4 alkyl carboxylester group and compounds suitable in the process.

Disclosed is a method for preparing a 1,3-dicarbonyl compound based on a metal hydride/palladium compound system. The method includes the following steps: suspending a palladium compound and a metal hydride in a solvent under the protection of nitrogen, then adding an electron-deficient olefin compound, reacting same at 0° C.-100° C. for 0.3 to 10 hours, then adding a saturated ammonium chloride aqueous solution to stop the reaction, and then subjecting same to extraction, evaporation until dryness, and column chromatography purification to obtain the 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used by the present invention are reagents easily obtained in a laboratory. Compared to a common hydrogen hydrogenation method, the method is easier to operate, and has a higher safety, mild conditions, and a high reaction yield.

Disclosed is a method for preparing a 1,3-dicarbonyl compound based on a metal hydride/palladium compound system. The method includes the following steps: suspending a palladium compound and a metal hydride in a solvent under the protection of nitrogen, then adding an electron-deficient olefin compound, reacting same at 0° C.-100° C. for 0.3 to 10 hours, then adding a saturated ammonium chloride aqueous solution to stop the reaction, and then subjecting same to extraction, evaporation until dryness, and column chromatography purification to obtain the 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used by the present invention are reagents easily obtained in a laboratory. Compared to a common hydrogen hydrogenation method, the method is easier to operate, and has a higher safety, mild conditions, and a high reaction yield.