HCID 10578596, compound → HCID 386444, compound

Participants

Reaction Steps

Pd(OH)2 --C(20%, 1.0 g) was added carefully under argon atmosphere to a solution of estradiol (7) (1.0 g, 1.8 mmol) in anhydrous THF (50 mL). The resulting mixture was hydrogenated at 45-50 psi on a Parr apparatus for 24 h. The catalyst was removed by filtration using a celite pad under argon atmosphere, and the pad was washed with dichloromethane (200 mL). Evaporation of the filtrate under reduced pressure, followed by purification on a silica gel column, gave compound (9) (0.5 g, 75%): mp 167-168° C.; IR (KBr) 3550, 2960-2840, 1590, 1510, 870 cm-1 ; 1H NMR (CDCl)3 δ 0.80 (s, 3H), 1.10-2.40 (m, 13H), 2.70-2.85 (m, 2H), 3.75 (m, 1H), 4.40 (q, J=8.5 Hz, 2H), 5.35 (s, 1H, OH), 5.5 (s, 1H), 6.70 (s, 1H), 6.80 (s, 1H); MS m/z (relative intensity) 370 (100), 311 (9), 270 (8), 244 (8), 205(6). Anal. (C20H25O3 0.7 H2O) C, H.

Provenance & Evidence