METHOD FOR PRODUCING A CONJUGATED Z-ALKEN-YN-YL ACETATE

摘要

Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ω-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).;

主权项

1. A method for producing a conjugated Z-alken-yn-yl acetate, comprising the steps of:
hydrolyzing an ω-halo-1,1-dialkoxy-2-alkyne represented by formula (2): wherein R1 and R2 are the same or different and each represents a linear, branched or cyclic C1-10 hydrocarbon group, X represents a halogen atom, and n stands for an integer of from 2 to 15,into a ω-halo-2-alkynal represented by formula (1):in water and an organic solvent in the presence of sulfonic acid.
reacting the ω-halo-2-alkynal with an alkylidene triphenylphosphorane represented by formula (3):
RCH═PPh3   (3)wherein R represents a linear branched or cyclic C1-12 hydrocarbon group and Ph represents a phenyl group,through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide represented by formula (4):and
acetoxylating the conjugated Z-alken-yn-yl halide into a conjugated Z-alken-yn-yl acetate represented by formula (5): wherein R represents a linear, branched or cyclic C1-12 hydrocarbon group.