HCID 9947892, compound → HCID 69789399, compound

Participants

Reaction Steps

Phenyltrimethylammonium tribromide (2.28 g) was added in small portions and in 10 min. to a solution of (14β,17α)-17-(hydroxymethyl)estr-5(10)en-3-one (Example 2; 1.75 g) in dry pyridine (47 ml). After 1.5 h stirring at room temperature the mixture was poured into ice-water and the product was extracted into ethyl acetate. The combined organic phases were washed with a saturated aqueous solution of sodium thiosulfate, water, a saturated aqueous solution of sodium hydrogencarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography provided (14β,17α)-17-(hydroxymethyl)estra-4,9-dien-3-one (0.36 g), [α]D20=−241 (c=1, dioxane).

Provenance & Evidence