Hydrochloric Acid → HCID 10050846, compound

Temperature

-78 °C

A 1.6 M solution of n-BuLi (17.5 mL) in hexanes was added dropwise by syringe under argon atmosphere at -78° C. to a solution of estradiol (4) (5.88 g, 11.2 mmol) in anhydrous THF (150 mL), and the resulting reaction mixture was stirred at -78° C. for 2 h. Anhydrous DMF (5.5 mL) was added and the stirring was continued for 1 h at -78° C. The mixture was warmed to 0° C. and stirred for 1 h, and poured onto an ice-cold solution of 3N HCl (100 mL). The aqueous layer was extracted with ether (3×300 mL). The combined organic layer was washed with 50% brine-water (100 mL), brine (150 mL), and dried over anhydrous sodium sulfate. The organic layer was filtered and evaporated under reduced pressure to afford impure estradiol (2), which was purified over a silica gel column using hexane-ethyl acetate as eluant. Appropriate fractions were combined and evaporated under reduced pressure to afford estradiol (2) (4.36 g, 82%): mp 145-147° C.; IR (KBr) 2920, 2820, 1675, 1600, 728, 685 cm-1, 1H NMR (CDCl3) δ 0.88 (s, 3 H), 1.1-2.5 (m, 13 H), 2.80-2.97 (m, 2 H), 3.50 (t, J=8.5 Hz, 1 H), 4.56 (s, 2 H), 5.65 (s, 2 H), 6.75 (s, 1H), 7.20-7.50 (m, 10 H), 7.78 (s, 1 H), 10.5 (s, 1 H). Anal. (C34H40O3)C,H.

1. customthe resulting reaction mixture
2. waitthe stirring was continued for 1 h at -78° C
3. temperatureThe mixture was warmed to 0° C.
4. stirringstirred for 1 h
5. extractionThe aqueous layer was extracted with ether (3×300 mL)
6. washThe combined organic layer was washed with 50% brine-water (100 mL), brine (150 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationThe organic layer was filtered
9. customevaporated under reduced pressure

ORD record

ord-65056abff1d54be098a344d46c88f97a

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06054598