Sodium Chloride → HCID 66846001, compound

Participants

Reaction Conditions

Reaction Steps

121 g triphenylphosphine, 27.1 g 4-nitrobenzoic acid, and 30.9 ml azodicarboxylic acid diisopropyl ester are added to a solution of 43.9 g of 3-methoxy-17β-hydroxyestra-1,3,5(10),15-tetraene in 1.6 l tetrahydrofuran and it is stirred for 23° C. for 2 hours. Saturated sodium chloride solution is added, it is extracted with ethyl acetate, the combined organic extracts are washed with saturated sodium chloride solution and dried over sodium sulfate. The residue obtained after filtration and evaporation of the solvent is taken up in 1.2 l acetone, 80 ml of 30% hydrogen peroxide solution is added while cooling, and after 20 minutes it is poured, while cooling, into 600 ml of semiconcentrated sodium thiosulfate solution. It is extracted with ethyl acetate, the combined organic extracts are washed with saturated sodium chloride solution and dried over sodium sulfate. The residue obtained after filtration and evaporation of the solvent is purified by recrystallization. 52.5 g of the title compound is isolated.

Provenance & Evidence