Benzene → HCID 54262875, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7.08 g of (1R, trans) 2,2-dimethyl-3-cyclopentylidenemethyl-cyclopropane-1-carboxylic acid chloride in 3 ml of benzene was added over 10 minutes at 28° C. to a suspension of 5 g of 1S-hydroxy-2-methyl-3-allyl-4-methylene-cyclopent-2-ene in 15 ml of benzene and 2.96 ml of pyridine and the mixture was stirred at 20° C. for 17 hours. 20 ml of water were added to the mixture which was stirred for 10 minutes and the decanted aqueous phase was extracted with benzene. The combined organic phases were washed with water and the wash waters were extracted with benzene. The combined organic phases were dried over magnesium sulfate and were filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 95-5 cyclohexane-ethyl acetate mixture containing 1‰ triethylamine to obtain 8.24 g of (1S) 2-methyl-3-allyl-4-methylene-cyclopent-2-ene-1-yl (1R, trans) 2,2-dimethyl-3-cyclopentylidienemethyl-cyclopropane-1-carboxylate with a specific rotation of [α]D20 =-87°±1° (c=0.9% in ethanol).

Provenance & Evidence