Thiophenol → HCID 70400272, compound

Participants

Reaction Conditions

Reaction Steps

To a magnetically stirred solution of triphenylphosphine (1.05 g) in dry tetrahydrofuran (15.0 ml) maintained at 0° C. was added diethylazodicarboxylate (0.488 ml) and the mixture was stirred at 0° C. for thirty minutes. To this stirred solution at 0° C. was added dropwise, a mixture of (11β,17β)-11-(acetyloxy)-9-fluoro-17-hydroxyandrosta-1,4-dien-3-one (362 mg, 1 mmole) and thiophenol (0.276 ml) dissolved in 5.0 ml of tetrahydrofuran. The solution was added over a ten minute period and then the reaction mixture stirred for 1 hour at 0° C., followed by 5.5 hours at room temperature. TLC (silica gel, 7:3 chloroform:ethyl acetate) indicated very little reaction taking place so the mixture was refluxed under nitrogen for 48.0 hours, followed by quenching in water and extraction with chloroform (4×50 ml). The combined chloroform extracts were dried over anhydrous magnesium sulfate and evaporated to a yellow oil. This was dissolved in a mixture of chloroform and hexane (8:2) and preadsorbed on silica gel. Flash chromatography was performed and the desired product was successfully eluted with (9:1) chloroform:hexane. The product-containing fractions were pooled, evaporated to an oil, taken up in hot ethyl acetate and evaporated to a yellow crystalline material which was vacuum dried.

Provenance & Evidence