Dehydroepiandrosterone → Androst-5-ene-3,17-dione

Participants

Reaction Steps

A mixture of 3β-hydroxyandrost-5-en-17-one (13.0 g) and IBX (25.3 g) in THF (260 mL) was heated at reflux under stirring for 4 h. After cooling to room temperature, the mixture was filtered and the solid washed with EtOAc (3×50 mL). The filtrate was evaporated to dryness. The residue was taken up with CH2Cl2 and the suspension filtered. The filtrate was evaporated to dryness and the residue triturated with Et2O/MeOH 9/1 (65 mL). After filtration and drying under vacuum, 5-androstene-3,17-dione (8.68 g, 67%) was obtained. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 5.40 (m, 1H), 3.41 (m, 1H), 2.76-1.06 (m, 18H), 1.29 (s, 3H), 0.91 (s, 3H).

Provenance & Evidence