Potassium Hydroxide → 13-(2-Chlorovinyl)-10-methyl-gon-5-ene-3beta,17beta-diol

Participants

Reaction Conditions

Reaction Steps

After adding 66 ml of a 10% strength aqueous potassium hydroxide solution, a solution of 1.68 g of 3β,17β-diacetoxy-13-(2-chlorovinyl)-10-methyl-gon-5-ene (a mixture of the cis and trans isomers in a ratio of 1:3) in 132 ml of methanol is stirred for 90 minutes at 45° C whilst passing nitrogen through the mixture. The reaction mixture is then concentrated to about 40 ml in a water pump vacuum and taken up in ethyl acetate. The organic phase, which is separated off, is washed with 1 N hydrochloric acid and with water until neutral, dried and evaporated. Chromatography on silica gel using a mixture of hexane/ethyl acetate (2:1) as the eluant gives 13-(2-chlorovinyl)-10-methyl-gon-5-ene-3β,17β-diol (a corresponding mixture of the cis and trans isomers) in an amorphous form.

Provenance & Evidence