Hydrochloric Acid → HCID 56609273, compound

Participants

Reaction Steps

0.3 ml of 30% aqueous hydrogen peroxide was added to a solution of 75 mg (226 micromol) of 4-(2-octenyl)-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone in 3 ml of methanol under ice cooling and stirring, and then 70 microliters of 1N sodium hydroxide was added. The mixture was stirred at 0° C. for 20 minutes. A saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with hexane. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The dried product was filtered and concentrated to give an oily product. The product was dissolved in 3 ml of acetone, and 0.5 ml of concentrated hydrochloric acid was added. The mixture was stirred for one hour. A saturated aqueous solution of sodium hydrogen carbonate was added, and the mixture was extracted with ethylacetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The dried product was filtered, concentrated and subjected to silica gel column chromatography (silica gel, 10 g; eluent, cyclohexane:ethylacetate=10:1) to give 45 mg (yield 54%) of 2-chloro-4-(2-octenyl)-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone.

Provenance & Evidence