4-Toluenesulfonyl chloride → HCID 53971946, compound

Participants

Reaction Steps

The 3β-(methoxyethoxymethoxy)-5-cholenic acid methyl ester was reduced with Vitride as described for the tetrahydropyranyl ether in Example 3. The resulting compound, the 3β-(methoxyethoxymethoxy)-24-hydroxy-5-cholene, was treated with tosyl chloride in pyridine and the 3β-(methoxyethoxymethoxy)-24-tosyloxy-5-cholene obtained. The tosyloxy compound was heated in dimethylformamide with potassium cyanide, and the tosyloxy group exchanged for the cyano group. 2.1 mmole of the 3β-(methoxyethoxymethoxy)-25-cyano-5-cholene was stirred with 2.36 g (10.5 mmole) of zinc bromide in 15 ml of methylene chloride. The insoluble material was removed by filtration, washed with ether, and the combined filtrates extracted with saturated aqueous solutions of sodium bicarbonate and sodium chloride. After drying, the solvents were evaporated, and the residue sponified with alkali. The 3β-hydroxy-5-homocholenic acid was obtained from the acidified saponification mixture.

Provenance & Evidence