Benzyl mercaptan → 21-Benzylthio-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Participants

Reaction Steps

Toluene-α-thiol (1.0 ml.) was added to a warm solution of sodium (0.6 g.) in a mixture of propan-2-ol (25 ml.) and toluene (30 ml.). 21-Bromo-3α-hydroxy-5α-pregnane-11,20 -dione (0.7 g.) was then added and the mixture was gently refluxed for 2 hr. The mixture was then partitioned between water and ether and the organic layer was washed with water, dried (Na2SO4) and evaporated. The residue was purified by preparative t.l.c. (CHCl3) to give title compound (0.4 g.) as a white foam, [α]D + 89° (c 1.1).

Provenance & Evidence