4-Toluenesulfonyl chloride → HCID 86738209, compound

Participants

Reaction Steps

To a solution of 1.80 g (6.0 mmol) (Z)-pregna-5,17(20)-dien-3β-ol in 8 ml of pyridine under a nitrogen atmosphere was added 1.26 g (6.6 mmol) of p-toluenesulfonyl chloride. Precipitation (pyridinium hydrochloride) began after 3 hr. After 19 hr., an additional 1.03 g (5.4 mmol) of p-toluenesulfonyl chloride was added. The reaction was left stirring for 5 days and then was poured into a stirred solution of 150 ml of 5% aqueous sodium bicarbonate cooled to 7°. After 30 min., the precipitate was removed by filtration, the filter cake washed with 2×15 ml of water and then dried over night to a vacuum dessicator (Drierite) at about 1 mm Hg to afford 2.50 g (92%) of crude product suitable for the next step. (Unstable to chromatography). An analytical sample was recrystallized from hexane to give (Z)-pregna-5,17(20)-dien-3β-ol-p-toluenesulfonate as white crystals, mp 119°-119.3°.

Provenance & Evidence