METHOD OF PRODUCING (4E)-TRIDEC-4-EN-1-YLACETATE Russian patent published in 2015 - IPC C07C69/145 C07C67/14 

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry and particularly to a method of producing (4E)-tridec-4-en-1-ylacetate. (4E)-tridec-4-en-1-ylacetate is a sex pheromone for tomato moth (Keiferia lycopersicella), which is a dangerous pest for solanaceae. Results of the invention can be useful in chemistry and agriculture. The method of producing (4E)-tridec-4-en-1-ylacetate includes alkylating malonic ester with (E)-1,3-dichloropropene to obtain diethyl[(2E)-3-chloroprop-2-en-1-yl]propanedioate, decarbalkoxylating diethyl[(2E)-3-chloroprop-2-en-1-yl]propanedioate to obtain ethyl(4E)-5-chloropent-4-enoate, Fe-catalysed cross-coupling of the ethyl(4E)-5-chloropent-4-enoate with octylmagnesium bromide to obtain ethyl(4E)-tridec-4-enoate, reducing the ethyl(4E)-tridec-4-enoate to obtain (4E)-tridec-4-en-1-ol, acetylation of the (4E)-tridec-4-en-1-ol to obtain (4E)-tridec-4-en-1-ylacetate. According to the invention, Fe-catalysed cross-coupling of ethyl(4E)-5-chloropent-4-enoate with octylmagnesium bromide to obtain ethyl(4E)-tridec-4-enoate is carried out in the presence of a Fe(acac)₂Cl catalyst in a mixture of tetrahydrofuran and N-methylpyrrolidone, wit the following molar ratio of reactants [(ethyl(4E)-5-chloropent-4-enoate]:[octylmagnesium bromide]:[Fe(acac)₂Cl]:[tetrahydrofuran ]:[N-methylpyrrolidone]=1:1.15:0.01:12:7 for 30 min at 0-5°C.

EFFECT: advantage of the disclosed method is higher output of (4E)-tridec-4-en-1-ylacetate.

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