Potassium Hydroxide → HCID 386752, compound

Participants

Reaction Steps

A 20% solution of KOH in methanol (5 mL) was added drcpwise to a suspension of estradiol (7) (0.95 g, 2.3 mmol) in anhydrous methanol (12 mL). The resulting reaction mixture was stirred at room temperature for 4 h. The solvent was removed under reduced pressure at 42-45° C. The residue was diluted with ice-water mixture (30 mL), and extracted with ethyl acetate (3×125 mL). The combined organic layer was washed with ice-cold water (30 mL), brine (30 mL) and dried over anhydrous sodium sulfite. The organic layer, on evaporation under vacuum, gave estradiol (10) (0.7 g, 92%). An analytical sample was prepared by a short column chromatography on silica gel using EtOAc, followed by EtOAc--MeOH (18:1), and finally chloroform: mp 194-196° C.; IR (KBr) 3400-3200, 2960-2842, 1650, 1590, 1500, 890, 852 cm-1 ; 1H NMR (DMSO-d6 +D2O) δ 0.85 (s, 3 H), 1.20-1.80 (m, 10 H), 1.82-2.82 (m, 8 H), 3.72 (t, J=8.5 Hz, 1 H), 4.20 (q, J=6.4 Hz, 2 H), 6.85 (s, 1 H), 7.58 (s, 1 H). Anal. (C20H26O4) C, H.

Provenance & Evidence