The present invention provides continuous flow processes for the preparation of the compound of Formula (2-A), an intermediate used in the preparation of zuclomiphene or a salt thereof. ##STR00001##

The present invention provides continuous flow processes for the preparation of the compound of Formula (2-A), an intermediate used in the preparation of zuclomiphene or a salt thereof. ##STR00001##

A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M.sup.1 represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X.sup.1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3). ##STR00001##

A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M.sup.1 represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X.sup.1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3). ##STR00001##

The present invention relates to a process for preparing a 3,7-dimethylalkane compound (3): wherein n is 5 or 6, the process comprising: subjecting a nucleophilic reagent, 2,6-dimethyloctyl compound (1): wherein M.sup.1 represents Li, Mg Z.sup.1, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 2,6-dimethyloctyl group, to a coupling reaction with an electrophilic alkyl reagent (2): wherein X.sup.1 represents a halogen atom or a p-toluenesulfonate group, and “n” is as defined above, to form the 3,7-dimethylalkane compound (3).

##STR00001##

The present invention relates to a process for preparing a 3,7-dimethylalkane compound (3): wherein n is 5 or 6, the process comprising: subjecting a nucleophilic reagent, 2,6-dimethyloctyl compound (1): wherein M.sup.1 represents Li, Mg Z.sup.1, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 2,6-dimethyloctyl group, to a coupling reaction with an electrophilic alkyl reagent (2): wherein X.sup.1 represents a halogen atom or a p-toluenesulfonate group, and “n” is as defined above, to form the 3,7-dimethylalkane compound (3).

##STR00001##

A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M.sup.1 represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X.sup.1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).

##STR00001##

A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M.sup.1 represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X.sup.1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).

##STR00001##

The present invention relates to a process for preparing a 3,7-dimethylalkane compound (3): wherein n is 5 or 6, the process comprising: subjecting a nucleophilic reagent, 2,6-dimethyloctyl compound (1): wherein M.sup.1 represents Li, Mg Z.sup.1, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 2,6-dimethyloctyl group, to a coupling reaction with an electrophilic alkyl reagent (2): wherein X.sup.1 represents a halogen atom or a p-toluenesulfonate group, and “n” is as defined above, to form the 3,7-dimethylalkane compound (3). ##STR00001##

The present invention relates to a process for preparing a 3,7-dimethylalkane compound (3): wherein n is 5 or 6, the process comprising: subjecting a nucleophilic reagent, 2,6-dimethyloctyl compound (1): wherein M.sup.1 represents Li, Mg Z.sup.1, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 2,6-dimethyloctyl group, to a coupling reaction with an electrophilic alkyl reagent (2): wherein X.sup.1 represents a halogen atom or a p-toluenesulfonate group, and “n” is as defined above, to form the 3,7-dimethylalkane compound (3). ##STR00001##