Sulfuric Acid → HCID 56635183, compound

Participants

Reaction Steps

A portion (17.23 ml) of a solution of concentrated sulphuric acid (0.4 ml) in isopropenyl acetate (20 ml) was added dropwise to a solution of 2β-hydroxy-5α-androstan-17-one (27.57 g) in isopropenyl acetate (140 ml). The solvent was removed slowly by distillation through a Vigreux column at such a rate that the solution was concentrated to approx. 60 ml after 6 h. The reaction mixture was cooled in an ice-bath to give a crystalline product, which was filtered off and washed with hexane (300 ml). The crop (33.21 g) in toluene was filtered through a column of silica gel (660 g; 0.2-0.5 mm); the eluate was evaporated to dryness and the residue was crystallised from acetone to afford 5α-androst-16-ene-2β,17-diol diacetate (24.38 g), m.p. 133°-134° C.; [α]D +34.4° (c 0.61 in CHCl3).

Provenance & Evidence