Sodium Iodide → HCID 56610066, compound

Participants

Reaction Steps

Second process. A solution of 23.4 g of (20S)-1α,3β-diacetoxy-20-methyl-21-p-toluenesulphonyloxy-pregn-5-ene in 260 ml of toluene is treated with 1.04 g of hexadecyl-tri-n-butyl-phosphonium bromide and a solution of 132 g of sodium iodide in 260 ml of water and the mixture is heated under reflux for 5 hours. After cooling, the organic phase is separated, washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated at 30°/11 Torr. Chromatography of the residue on 270 g of silica gel with hexane/ether (19:1 and 9:1) gives 21.1 g of product of melting point 135°-136°. After recrystallization from concentrated pentane solution, there are obtained 16.0 g of product of melting point 136°; [α]D20 =-11.0° (c=1.0 in CHCl3).

Provenance & Evidence