Acetic Acid → 3-Methoxycarbonylmethyl-2-(2-pentynyl)cyclopentanol

Participants

Reaction Conditions

Reaction Steps

4-Methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (890 mg) and 350 mg of sodium borohydride are dissolved in 20 ml of methanol, and the mixture is refluxed at 80° C. for one hour. On completion of the reaction, the mixture is cooled to room temperature. With addition of 60 ml of acetic acid, the mixture is stirred for 30 minutes and thereafter concentrated in a vacuum. The residue is purified with a silica gel column and distilled in a vacuum, affording 3-methoxycarbonylmethyl-2-(2-pentynyl)cyclopentanol (compound (1), R2 =CH3) in a yield of 94%, b.p. 65°-69° C./0.15 mm Hg.

Provenance & Evidence