Potassium Carbonate → HCID 10578596, compound

Participants

Reaction Conditions

Reaction Steps

Powdered K2CO3 (1.5 g, 11 mmol) was added to a solution of estradiol (6) (4.0 g, 8.5 mmol) in anhydrous DMF (50 mL) followed by dropwise addition of CF3CH2I (5.0 mL, 51 mmol) at room temperature. The resulting reaction mixture was heated at 110° C. for 3 h. Additional K2CO3 (2.5 g) and CF3CH2I (6 mL) were added, and the mixture was heated again at 130° C. for 2 h. The mixture was cooled in an ice bath and poured onto ice cold 3N HCl (125 mL). The aqueous layer was extracted with ether (2×200 mL). The combined ether layer was washed with 3N HCl (100 mL), water (100 mL), brine (100 mL), and dried over anhydrous MgSO4. The ether layer was evaporated under reduced pressure and the resulting crude product on purification on a silica gel column gave estradiol (7)(4.5 g, 95%) as a colorless oil: IR (neat) 2910, 2850, 1600, 1500, 730, 690 cm-1 ; 1H NMR (CDCl3) δ 0.9 (s, 3H), 1.1-2.4 (m, 13H), 2.65-2.85 (m, 2H), 3.50 (t, J=8.5 Hz, 1H), 4.40 (q, J=8.5 Hz, 2H), 4.56 (s, 2H), 5.05 (s, 2H), 6.70 (s, 1H), 6.98 (s, 1H), 7.2-7.55 (m, 10H). Anal. (C34H37F3O3) C, H.

Provenance & Evidence