Acetic Acid → HCID 11796064, compound

Participants

Reaction Conditions

Reaction Steps

A solution of chromium trioxide (1.6 g, 16 mmol) in 90% glacial acetic acid (7.5 mL) was added dropwise at 15° C. to a solution of 2-ethoxy-3,17β-diacetyl derivative (5), (1.5 g, 3.7 mmol) in glacial acetic acid (12 mL). The resulting mixture was stirred at 15° C. for 35 min. The mixiure was poured onto ice-water mixture (150 mL) and compound was extracted into ethyl acetate (3×180 mL). The combined organic layer was washed with water (100 mL), NaHCO3 solution (100 mL), water (100 mL), brine (100 mL), and dried over anhydrous sodium sulfate. The organic layer, upon evaporation under reduced pressure, provided a crude compound, which on purification on a silica gel column using hexane: ethyl acetate mixture aas eluant gave 1.20 g (55%) of estradiol (7): mp 195° C.; IR (KBr) 2980-2810, 1765, 1730, 1715, 1665, 1600, 1500, 918, 880 cm-1 ; 1H NMR (CDCl3) δ 0.89 (s, 3 H), 1.30-1.85 (m, 9 H), 1.90-2.45 (m, 11 H), 2.47-2.85 (m, 2 H), 4.15 (q, J=6.4 Hz, 2 H), 4.78 (t, J=8.5 Hz, 1 H), 6.95 (s, 1 H), 7.77 (s, 1 H). Anal. (C24H30O6) C, H.

Provenance & Evidence