Thiophenol → HCID 69874424, compound

Participants

Reaction Steps

i)—A solution of (7α,14β,15β,17α)-17-(hydroxymethyl)-7-methyl-14,15-methyleneestr-4-en-3-one (Example 1, 0.40 g) in a mixture of formaldehyde (37 wt. % solution in water, 0.24 ml), triethylamine (0.288 ml), thiophenol (0.276 ml) and ethanol (0.721 ml) was stirred at room temperature overnight. The reaction mixture was poured into a aqueous solution of potassium hydroxide (0.5 M) and the product was extracted into ethyl acetate. The combined organic phases were washed with a aqueous solution of potassium hydroxide (0.5 M) and brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded (7α,14β,15β,17α)-17-(hydroxymethyl)-7-methyl-4-[(phenylthio)methyl]-14,15-methyleneestr-4-en-3-one (0.13 g).

Provenance & Evidence