Pyridine → 2-chloro-6-fluorobenzyl(+/-)-cis-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of (±)-cis-1-chlorocarbonyl-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane (0.82 g), 2-chloro-6-fluorobenzyl alcohol (1.0 g), pyridine (0.275 g) and dry toluene (50 ml) was stirred at the ambient temperature (ca. 25° C.) for a period of 6 hours and then kept for a further period of 72 hours without stirring. The mixture was diluted with diethyl ether (350 ml) and the resultant mixture washed with water, with dilute aqueous sodium carbonate solution, and then dried over anhydrous magnesium sulphate. The solvents were evaporated and the residual oil purified by preparative thick layer chromatography using silica gel plates and diethyl ether as eluent. The oil which was obtained was then distilled to yield 2-chloro-6-fluorobenzyl(±)-cis-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylate (0.67 g) b.p. 150°/0.05 mm Hg.

Provenance & Evidence