Hydrochloric Acid → HCID 56609317, compound

Participants

Reaction Steps

17 mg (51 mmol) of 4-octyl-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone was dissolved in 1 ml of dichloromethane and 23 μl (280 μmol) of pyridine was added thereto. With stirring, 49 mg (254 mmol) of phenyl selenium chloride was added to the mixture and the reaction mixture was refluxed. 10 hours later, 23 μl (280 mmol) of pyridine and 49 mg (254 mmol) of phenyl selenium chloride were further added and the mixture was refluxed for 25 hours. 0.5 ml of pyridine was added to the reaction mixture and then, with vigorous stirring, 35% aqueous hydrogen, peroxide was further added and the mixture was stirred for another 1 hour. Hydrochloric acid and water were added thereto for extraction and the aqueous layer was then extracted twice with dichloromethane. The organic layer was washed first with a saturated aqueous solution of sodium hydrogencarbonate and then with a saturated saline solution and dried over sodium sulfate anhydride. Thereafter, it was filtrated, concentrated, and chromatographed on a column of silica gel (silica gel 5 g; eluent, hexane:ethyl acetate=30:1→10:1) to obtain 10 mg (yield 53%) of 2-chloro-4-octyl-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone.

Provenance & Evidence