Potassium Carbonate → Oct-2-ene

Participants

Reaction Steps

1.25 g of the mixture of 3-(1,1-methylene-5-acetoxypentyl)-6β-[3α-(2-tetrahydropyranyloxy)-5(R),9-dimethyl-1,8-decadienyl]-7α-(2-tetrahydropyranyloxy)bicyclo[3.3.0]oct-2-ene and its oct-3-ene isomer (prepared as described in Example 8) was dissolved in 30 ml of methanol. 0.25 g of anhydrous potassium carbonate was added to the mixture, and the mixture was stirred for 2.5 hours at room temperature. The reaction mixture was then diluted with 150 ml of water, and the solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was subjected to medium pressure liquid chromatography using a Lobar (trade mark) column (size C), eluted with a 1:2 by volume mixture of ethyl acetate and hexane, yielding 0.68 g of the oct-2-ene compound and 0.51 g of the oct-3-ene compound.

Provenance & Evidence