1-(2-acyloxyethyl)cyclopropyl sulfonate compound, 3-halomethyl-3-butenyl carboxylate compound, and method for producing 4-alkyl-3-methylenebutyl carboxylate

摘要

Provided is a simple, selective and efficient method for producing 4-alkyl-3-methylenebutyl carboxylates such as 7-methyl-3-methylene-7-octenyl propionate. More specifically, provided is, for example, a method for producing a 4-alkyl-3-methylenebutyl carboxylate compound, comprising an acyloxylation step of subjecting a 1-(2-haloethyl)cyclopropyl sulfonate compound (1) to acyloxylation to obtain a 1-(2-acyloxyethyl)cyclopropyl sulfonate compound (2), a halogenation step of subjecting the compound (2) to halogenation involving cyclopropyl-allyl rearrangement to obtain a 3-halomethyl-3-butenyl carboxylate compound (3), and a coupling step of subjecting the compound (3) to a coupling reaction with an organometallic reagent (4) to obtain the 4-alkyl-3-methylenebutyl carboxylate compound (5).;

主权项

1. A method for producing a 4-alkyl-3-methylenebutyl carboxylate compound, the method comprising:
an acyloxylation step of subjecting a 1-(2-haloethyl)cyclopropyl sulfonate compound represented by General Formula (1): wherein X1 represents a halogen atom and Z represents a monovalent hydrocarbon group having 1 to 10 carbon atoms and optionally containing one or more unsaturated bonds, to acyloxylation to obtain a 1-(2-acyloxyethyl)cyclopropyl sulfonate compound represented by General Formula (2): wherein R1 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms and optionally containing one or more unsaturated bonds, a halogenation step of subjecting the 1-(2-acyloxyethyl)cyclopropyl sulfonate compound (2) to halogenation involving cyclopropyl-allyl rearrangement to obtain a 3-halomethyl-3-butenyl carboxylate compound represented by General Formula (3): wherein X2 represents a halogen atom, which may be the same as or different from X1,and
a coupling step of subjecting the 3-halomethyl-3-butenyl carboxylate compound (3) to a coupling reaction with an organometallic reagent represented by General Formula (4):
R2M   (4)wherein R2 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms and optionally containing one or more unsaturated bonds, which may be the same as or different from R1, andM represents a cationic moiety,to obtain the 4-alkyl-3-methylenebutyl carboxylate compound represented by Formula (5):