Hydrochloric Acid → HCID 54246591, compound

Participants

Reaction Steps

To a solution of 450 mg (1.29 mmol) of (4S)-2,3-epoxy-4-(1-octenyl)-5-(6-methoxycarbonylhexylidene)cyclopentenone in 12 ml of acetone was added 2 ml of concentrated hydrochloric acid at room temperature under stirring. The mixture was stirred for 2 hours. A saturated aqueous solution of sodium hydrogencarbonate was added, and the mixture was concentrated. The product 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 filtered, concentrated and subjected to silica gel column chromatography (silica gel, 40 g; eluent, hexane:ethyl acetate=10:1→5:1) to give 19 mg (yield 4%) of a less polar isomer (Z-form) of (4R)-2-chloro-4-(1-octenyl)-5-(6-methoxycarbonylhexylidene)cyclopentanone and 177 mg (yield 37%) of a more polar isomer (E-form).

Provenance & Evidence