Dicyclohexylcarbodiimide → (RS)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylate

Participants

Reaction Conditions

Reaction Steps

2.06 g of dicyclohexylcarbodiimide were added at 0° C. to a solution of 1.52 g (1R,cis) 2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylic acid in 30 ml of methylene chloride followed by the addition of a few crystals of 4-dimethylamino-pyridine after which the mixture was stirred at 0° C. for 15 minutes. A solution of 2.47 g of (RS)α-cyano-3-phenoxy-benzyl alcohol in 10 ml of methylene chloride was added to the mixture which was stirred at 20° C. for 4 hours and was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 3-7 benzene-petroleum ether (b.p.=35° to 70° C.) mixture and then with a 7-3 benzene-petroleum ether (b.p.=35° to 70° C.) mixture yielded 2.89 g of (RS)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylate.

Provenance & Evidence