METHOD OF OBTAINING (13Z)-ACOSE-13-EN-10-ONE Russian patent published in 2017 - IPC C07C45/68 C07C49/203 

FIELD: chemistry.

SUBSTANCE: invention relates to a process for the preparation of (13Z)-acose-13-en-10-one, which, in a 20:1 mixture with the minor component (12Z)-nonadec-12-en-9-one, is identified as the sexual pheromone of peach Moth-eaters of Casposina niponensis. The method consists in the fact that the double carbon-carbon bond of the (Z)-configuration is formed as a result of stereoselective Fe(acac)₃-catalyzed cross-coupling of ethyl (4Z)-5-chloropent-4-enoate with n-hexyl magnesium bromide in a mixture of tetrahydrofuran and N-methylpyrrolidone to give ethyl (4Z)-undec-4-enoate, then alkaline hydrolysis of ethyl (4Z)Undec-4-enoate to give (4Z)-undec-4-enoic acid, it is transformed into the acid chloride and a second Fe(acac)₃-catalyzed cross-combination of the obtained acid chloride with n-nonylmagnesium bromide.

EFFECT: method allows to obtain the target product at the key stage of cross-coupling with a higher yield.

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