3-Methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol → a Methyl jasmonate

Participants

Reaction Conditions

Reaction Steps

A 150 mg quantity of 3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol is dissolved in 10 ml of methylene chloride. A 2 ml quantity of chromic acid solution of 2 M concentration is added dropwise to the solution. The mixture is stirred at about 18° C. for 12 hours and thereafter extracted with ethyl acetate. The extract is washed with aqueous solution of sodium chloride, dried and concentrated. The residue is purified with a silica gel column and distilled in a vacuum, affording 3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanone (compound (4), R2 =CH3) in a yield of 88%, b.p. 92°-96° C./2.7 mm Hg.

Provenance & Evidence