Benzene → HCID 54262875, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5.4 g of (1R, trans) 2,2-dimethyl-3-(2-oxo-3-tetrahydrofuranylidenemethyl)-cyclopropane-1-carboxylic acid chloride in 50 ml of benzene was added at less than 25° C. over 15 minutes to a suspension of 3 g of (1S)-hydroxy-2-methyl-3-allyl-4-methylene-cyclopent-2-ene in 10 ml of benzene and 3 ml of pyridine at 20° C. and the mixture was stirred at 20° C. for 20 hours. 30 ml of water were added and the mixture was stirred for 15 minutes. The decanted aqueous phase was extracted with benzene and 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 7-3 cyclohexane-ethyl acetate mixture containing 1‰ triethylamine yielded 2.61 g of (1S) 2-methyl-3-allyl-4-methylene-cyclopent-2-ene-1-yl (1R, trans) 2,2-dimethyl-3-(2-oxo-3-tetrahydrofuranylidenemethyl)-cyclopropane-1-carboxylate with a specific rotation of [α]D20 =-28.5°±2.5° (c=0.5% in ethanol).

Provenance & Evidence