HCID 13371411, compound → HCID 13371413, compound

Participants

Reaction Steps

To a solution of 4-fluoroestra-1,3,5-(10)-trien-17β-ol IV as prepared in Example 2 (100 mg, 0.36 mmol) in 1.5 ml of acetone at 0° C. is added, dropwise with stirring, a solution of (95ml) of 8N chromium trioxide in ammonium sulfate. After approximately 5 min. the reaction mixture is poured into 75 ml of ice-water and the solids are collected. The filter cake is stirred with methanol, the inorganic salts are removed and the filtrate is evaporated to dryness to give the crude product, 4-fluoroestra-1,3,5-(10)-trien-17-one as a tan solid. The latter crystallizes from ether-petroleum ether (30°-60°) as a colorless solid (60 mg, 61% yield), mp 139°-141° C. Ir (KBr)cm-1 1724 (C17C=O), 1230 (aryl fluoride); 1H NMR δ7.21-6.81 (m, 3, H1, H2, H3 aromatic) 2.91-1.54 (m, 15), 0.92 (s, 3, C18CH3). Anal. Calc'd. for C, 79.38; H, 7.77; F, 6.98. Found: C, 79.53; H, 7.76; F, 7.13.

Provenance & Evidence