Benzene → HCID 54341468, compound

Participants

Reaction Steps

1.5 ml of pyridine were added at 5° C. to a mixture of 3 g of the product of Step A, 3 g of (1R, trans) 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane-carboxylic acid chloride and 50 ml of benzene and the mixture was held at 5° C. for 15 minutes, at 20° C. for 2 hours and was then poured into a mixture of 18 ml of 2 N hydrochloric acid and 100 ml of water at 5° C. The mixture was extracted with ether and the organic phase was washed with water, dried and evaporated to dryness. The 6.5 g of residue was chromatographed over silica gel and was eluted with a 97-3 toluene-ethyl acetate mixture to obtain 4.93 g of (1S) 2-methyl-3-allyl-4-cyanomethylene-cyclopent-2-ene-1-yl (1R, trans) 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α ]D20 =-162.5°±3.5° (c=0.6% in benzene).

Provenance & Evidence