Hydrogen Peroxide → HCID 56621154, compound

Participants

Reaction Steps

660 mg (2.37 mmol) of 4-butyl-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone was dissolved in 10 ml of methanol. With ice cooling and stirring, 1.2 ml of 30% aqueous hydrogen peroxide and then 0.23 ml of 1N sodium hydride were added to the solution and the mixture was stirred at 0° C. for 20 minutes. Saturated aqueous ammonium chloride was added thereto and was extracted with hexane. The organic layer was washed with a saturated saline solution, dried over sodium sulfate anhydride, filtered, concentrated, and chromatographed on a column of silica gel (silica gel, 30 g; eluent, hexane:ethyl acetate=10:1) to obtain 500 mg (yield 72%) of 2,3-epoxy-4-butyl-5-(6-methoxycarbonylhexylidene)cyclopentenone.

Provenance & Evidence