Thionyl Chloride → HCID 9797346, compound

Participants

Reaction Steps

6β-Propargyl-5α-hydroxyandrostane-3,17-dione (10) (0.3 mmol) was dissolved in dry pyridine (10 ml), cooled in an ice-bath and thionyl chloride was added. After stirring for 3-5 minutes, the reaction mixture was poured over ice-water, extracted with ethyl acetate, washed (water), dried, and evaporated in vacuo. The residue was subjected to column chromatography (hexane/ethyl acetate). Recrystallization from acetone/hexane gave the title compound (60% of the analytical product); m.p. 159°-160° C.; IR (KBr) 3245, 2120, 1734, and 1662 (C=O) cm-1 ; 1H-NMR (CDCl3) δ 0.93 (s, 3H, 18-CH3), 1.26 (s, 3H, 19-CH3), 2.6-2.8 (m, 1H), 5.84 (s, 1H, 4-H).

Provenance & Evidence