p-Toluenesulfonic acid → HCID 68147543, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5 g. of rac.-1,3-diacetoxy-8α-estra-1,3,5(10)-trien-17-one, 100 ml. of isopropenyl acetate, and 14.4 g. of p-toluenesulfonic acid is heated for 21 hours under a slight N2 stream to 105° C. After the mixture has been heated to 125° C., 50 ml. of isopropenyl acetate are gradually distilled off. After cooling, 10 ml. of pyridine is added, the mixture is diluted with methylene chloride, washed with saturated sodium bicarbonate solution and water, and dried over sodium sulfate. The solvent is evaporated under vacuum. After chromatography on 260 g. of SiO2, 3 g. of oily rac.-1,3,17-triacetoxy-8α-estra-1,3,5(10),16-tetraene is obtained, which is further processed as the crude product.

Provenance & Evidence