4-Toluenesulfonyl chloride → HCID 86586579, compound

Participants

Reaction Steps

A solution of 0.573 g toluene-4-sulfonylchloride in 4 ml pyridine was added drop by drop to a solution of 0.926 g (20S)-4,4,20-trimethyl-pregna-5,7-dien-3β,21-diol 3-benzoate in 15 ml pyridine while cooling on an ice-bath. The reaction mixture was stirred for 1 h at 0-3□C. and overnight at room temperature. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layers were combined, washed with 1N hydrochloric acid, saturated sodium hydrogencarbonate solution and brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 1.0 g of (20S)-4,4-dimethyl-20-[((toluene-4-sulfonyl)oxy)methyl]-pregna-5,7-dien-3β-ol benzoate which could be further purified by crystallization from methanol.

Provenance & Evidence