4-Toluenesulfonyl chloride → HCID 86746923, compound

Participants

Reaction Steps

A solution of 3α, 12α-dihydroxy-5β-chol-8(14)-en-24-ol (12.8 g) in methylene chloride/acetonitrile (1:1) (180 ml) is cooled to -5° C. Triethylamine (6 ml), 4-dimethylaminopyridine (0.435 g), and p-toluenesulfonyl chloride (6.65 g) are added and the solution stirred at 0° to 4° C. for about 18 hours. The solution is diluted with ethyl acetate/methanol (9:1), washed with brine and the organic solution dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography in ether, followed by 10% methanol in ethyl acetate to give the desired product.

Provenance & Evidence