Benzene → HCID 54284345, compound

Participants

Reaction Steps

8 g of (1R,cis) 2,2-dimethyl-3-cyclobutylidenemethyl-cyclopropane-1-carboxylic acid chloride and 10 ml of benzene were added at 10° C. to a solution of 50 ml of benzene, 4 g of isopropanol and 4 g of pyridine and the reaction mixture was stirred for 8 hours. The mixture was poured into iced water and the decanted organic phase was washed with water, with aqueous sodium bicarbonate solution, with water, with N hydrochloric acid and finally with water. The solution was dried and evaporated to dryness under reduced pressure at 45° C. The residue was chromatographed over silica gel and was eluted with an 8-2 petroleum ether (b.p.=60°-80° C.)-isopropyl ether mixture to obtain the fraction with an Rf=0.55. The solution was evaporated to dryness under reduced pressure at 45° C. to obtain 5 g of isopropyl (1R,cis) 2,2-dimethyl-3-cyclobutylidenemethyl-cyclopropane-1-carboxylate with a boiling point of 66°~68° C. at 0.1 mm Hg and a specific rotation of [α]D 20 =+74.5° (c=1% in chloroform).

Provenance & Evidence