Benzene → HCID 54262875, compound

Participants

Reaction Conditions

Reaction Steps

30 ml of a benzene solution of (1R, cis) 2,2-dimethyl-3-cyclopentylidenemethyl-cyclopropane-1-carboxylic acid chloride prepared from 7 g of the corresponding acid were added at 20° C. over 15 minutes to a mixture of 4 g of 1S-hydroxy-2-methyl-3-allyl-4-methylene-cyclopent-2-ene, 10 ml of benzene and 5 ml of pyridine and the mixture was stirred at 20° C. for 20 hours and was then poured into 30 ml of water. The mixture was stirred for 10 minutes and was then extracted with methylene chloride. The combined organic phases were washed with water, dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 95-5 cyclohexane-ethyl acetate mixture containing 1‰ triethylamine yielded 4.1 g of (1S) 2-methyl-3-allyl-4-methylene-cyclopent-2-ene-1-yl (1R, cis) 2,2-dimethyl-3-cyclopentylidenemethyl-cyclopropane-1-carboxylate.

Provenance & Evidence