9alpha-Hydroxyandrost-4-ene-3,17-dione → 9-Dehydroandrostenedione

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Reaction Steps

Following the general procedure of Example 6 but making non-critical variations, 9α-hydroxyandrostenedione (20.00 g.) is reacted with chlorosulfonic acid (10 ml.) at a reaction temperature of 1°-11°. Upon workup the reaction gives androsta-4,9(11)-diene-3,17-dione, 17.94 g., (89.7% weight yield, 95.2% chemical yield); m.p. 201°-204.5°; [α]D +217° (chloroform); UV (methanol) λmax = 240 nm (ε = 16,300).

Provenance & Evidence