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

Participants

Reaction Steps

A 5 q quantity of 5-methoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (compound (2-a)) and 1.35 g of sodium borohydride are dissolved in 200 ml of methanol, and the solution is refluxed in a nitrogen atmosphere for one hour. The reaction mixture is cooled to room temperature, and about 30 ml of acetic acid is added to the mixture. The resulting mixture is stirred for 30 minutes and thereafter concentrated in a vacuum. The residue is dissolved in a mixture of benzene and ethyl acetate, and the solution is purified with a silica gel column. After removing the solvent from the product, the product is distilled in a vacuum, affording 3-methoxycarbonylmethyl-2-methoxycarbonyl-2-(2-pentynyl)-cyclopentanol (compound (1-a), R1 =R2 +CH3) in a yield of 92.5%, b.p. 70-75° C./0.005 mm Hg.

Provenance & Evidence