Production procedure of an asymmetric conjugated diino compound and production process of a Z, Z-conjugated diene compound using the same

摘要

A process for the production of an asymmetric conjugated diino compound, comprising: a step of submitting a terminal alkyne compound represented by the formula (1): HC≡C-Z1-Y1 (1) in which Y1 represents an atom of hydrogen; a halogen atom; a hydroxyl group; a hydroxyl group protected with a protecting group that forms an ester, ether, or acetal; or a formyl group protected with a protecting group that forms thioacetal or acetal; and Z1 represents a linear, branched, cyclic, or polycyclic divalent C1-14 hydrocarbon group having an optional double bond or triple bond; to a coupling reaction with an alkynyl halide represented by the formula (2): Y2-Z2-C≡C-X (2) in which Y2 represents a hydrogen atom; a halogen atom; a hydroxyl group; a hydroxyl group protected with a protecting group that forms an ester, ether, or acetal; or a formyl group protected with a protecting group that forms thioacetal or acetal; Z2 represents a linear, branched, cyclic or polycyclic divalent C1-14 hydrocarbon group having an optional double bond or triple bond; X represents a halogen atom; and Y2-Z2 is not the same as Y1-Z1; by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diino compound represented by the formula (3): Y2-Z2-C≡CC≡C-Z1 -Y1 (3).