Dimethylformamide → 21-Chloro-20-methoxy-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one

Participants

Reaction Steps

20,21-Dichloro-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one (VII, Example 2, 1.0 g), dry DMF (20 ml) and methanol (4 ml) are stirred under nitrogen and cooled to -25°. Sodium methoxide in methanol (25%, 1 ml) is added dropwise. After 30 minutes, the mixture is quenched with water (0.33 ml) and allowed to warm to 20°-25°. The product is isolated by diluting the mixture with water and extracting with ethyl acetate. The organic layer is separated and dried over sodium sulfate and then concentrated under reduced pressure to give the title compound: NMR (CDCl3) 0.85, 0.87, 0.98, 1.36, 1.34, 3.89, 3.84, 5.03, 5.10, 5.23, 5.43, 5.53, 5.72, 5.75 and 7.4-8.0δ.

Provenance & Evidence