Chloranil → (17beta)-3-oxo-N-[2-(trifluoromethyl)phenyl]androsta-4,6-diene-17-carboxamide

Participants

Reaction Steps

A mixture of (17β)-3-oxo-N-[2-(trifluoromethyl)phenyl]androst-4-ene-17-carboxamide (2-1) (3.74 g, 8.14 mmol) and p-chloranil (2.40 g, 9.77 mmol) in t-butanol (40 mL) under N2 was heated to reflux for 90 min. The reaction was concentrated and the residue dissolved in EtOAc and washed with 0.5 N NaOH solution (2×60 mL), 10% KHSO4 solution, and brine. Upon removal of the solvent, the residue was purified by flash chromatography on silica gel (0 to 35% EtOAc-hexanes) to afford 5-2 as a brownish foam.

Provenance & Evidence