Hydrochloric Acid → HCID 70402744, compound

Participants

Reaction Steps

16 mg (46 microliters) of (4R)-2,3-epoxy-4-(1-octenyl)-5-(6-methoxylcarbonylhexylidene)cyclopentenone was dissolved in 1 ml of acetone. To the solution was added 0.1 ml of concentrated hydrochloric acid, and then the mixture was stirred for 30 minutes. A saturated aqueous solution of sodium hydrogencarbonate was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The dried product was concentrated and subjected to silica gel column chromatography (silica gel, 5 g; eluent, hexane:ethyl acetate=15:1→6:1) to give 11 mg (yield 65%) of (4S)-2-chloro-4-(1-octenyl)-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone.

Provenance & Evidence