METHOD OF PRODUCING 11(E)-TETRADECEN-1-YLACETATE Russian patent published in 2011 - IPC C07C69/07 C07C67/08 

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing 11(E)-tetradecen-1-ylacetate, which is sex pheromone of sod webworms, the basic component of pheromones of omnivorous leaf-roller moths, stem moths, fir leaf-roller moths and certain other types of dangerous pests, involving a Grignard reaction of acrolein with ethylmagnesium bromide to obtain 1-penten-3-ol, ortho-ether Claisen rearrangement with participation of 1-penten-3-ol and triethyl ortho-acetate to obtain ethyl ether of 4(E)-heptenoic acid, reduction of the ethyl ether of 4(E)-heptenoic acid to obtain 4(E)-hepten-1-ol, substitution of the hydroxyl group of 4(E)-hepten-1-ol with Br to obtain 1-bromo-4(E)-heptene, cross-coupling reaction of 1-bromo-4(E)-heptene with 7-[(tetrahydro-2H-pyran-2-yl)oxy]heptylmagnesium bromide in the presence of a catalyst to obtain 11(E)-tetradecen-1-ol, acetylation of 11(E)-tetradecen-1-ol to obtain 11(E)-tetradecen-1-ylacetate, in which cross-coupling of 1-bromo-4(E)-heptene with 7-[(tetrahydro-2H-pyran-2-yl)oxy]heptylmagnesium bromide to obtain 11(E)-tetradecen-1-ol is carried out in the presence of a Li₂CuCl₄ in the medium of tetrahydrofuran in the following molar ratio [1-bromo-4(E)-heptene]: [7-[(tetrahydro-2H-pyran-2-yl)oxy]heptylmagnesium bromide]:[ Li₂CuCl₄]:[tetrahydrofuran]=1:1.2:0.03:20 for 1 hour at temperature of minus 75°C, then for 1 hour at temperature ranging from minus 75°C to 20°C and for 10 hours at 20°C. Since the 1-2% content of the (Z)-isomer already inhibits attractive properties of 11(E)-tetradecen-1-ylacetate, existing methods are not suitable for practical application.

EFFECT: method is distinguished by stereoselectivity.

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