Dicyclohexylcarbodiimide → 5-benzyl-3-furyl-methyl (1R,cis)2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylate

Participants

Reaction Conditions

Reaction Steps

4.06 g of dicyclohexylcarbodiimide were added at 0° C. to a solution of 1.52 g of (1R,cis)2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane carboxylic acid in 40 ml of methylene chloride followed by addition of a few crystals of 4-dimethylaminopyridine and stirring at 0° C. for 15 minutes. A solution of 2.07 g of 5-benzyl-3-furyl-methanol in 10 ml of methylene chloride were added at 0° C. to the mixture which was stirred at 20° C. for 4 hours and was then filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 1-1 benzene-petroleum ether (b.p.=35° to 70° C.) yielded 2.72 g of 5-benzyl-3-furyl-methyl (1R,cis)2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylate.

Provenance & Evidence