Acetic Acid → HCID 54513106, compound

Participants

Reaction Steps

31 g of the mixture of E- and Z-isomes of 2-chloro-5-(6-methoxycarbonylhexylidene)-4-octyl-4-trimethylsilyloxy-2-cyclopentenone obtained in Example 2 was mixed with 3 ml of a 6:1:3 mixture of acetic acid, tetrahydrofuran and water, and the mixture was stirred for 2 hours. A saturated aqueous solution of sodium bicarbonate was added, and the mixture was extracted with ether. The extract was dried over anhydrous sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on a silica gel column to give 25 mg (yield 97%) of a mixture of Z- and E-isomers of 2-chloro-4-hydroxy-5-(6-methoxxycarbonylhexylidene-4-octyl-2-cyclopentenone.

Provenance & Evidence