Hydrochloric Acid → HCID 56622655, compound

Participants

Reaction Steps

300 mg (1.02 mmol) of 2,3-epoxy-4-butyl-5-(6-methoxycarbonylhexylidene)cyclopentenone was dissolved in 3 ml of acetone. 0.5 ml of concentrated hydrochloric acid was added to the solution and the mixture was stirred for 50 minutes. A saturated aqueous solution of sodium hydrogen carbonate was added thereto and was extracted with hexane. The organic layer was washed with a saturated saline solution, dried over sodium sulfate anhydride, filtrated, and subjected to column chromatography on silica gel (silica gel, 20 g; eluent, cyclohexane:ethyl acetate=10:1) to obtain 28 mg (yield 9%) of a less polar isomer (Z-form) of 2-chloro-4-butyl-5-(6-methoxycarbonyl-hexylidene)-2-cyclopentenone and 183 mg (yield 57%) of its more polar isomer (E-form).

Provenance & Evidence