反应详情

To a solution of enone 55 (0.35 g, 1.17 mmol) in acetonitrile (10 mL) was added a CuBr2 (0.31 g, 1.4 mmol) and stirred overnight at room temperature. Water was added until disappearance of the green color, and the acetonitrile was removed under reduced pressure. The residue was extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4, filtered, and the combined organic layers were washed with water; brine, dried over anhydrous MgSO4, filtered, and concentrated to afford a gum. Chromatography (20% EtOAc/hexane) yielded estrone 56 as a yellow solid (0.28 g, 80%): The major 7α-ethyl isomer of 56: 1H NMR (300 MHz, CDCl3) δ 0.91 (s, 3, CH3), 0.95 (t, J=7.3 Hz, 3, CH2CH3), 6.59 (d, J=2.5 Hz, 1, ArH), 6.65 (dd, J=2.5, 8.4 Hz, 1, ArH), 7.13 (d, J=8.4 Hz, 1, ArH).

1. customthe acetonitrile was removed under reduced pressure
2. extractionThe residue was extracted with EtOAc
3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
4. filtrationfiltered
5. washthe combined organic layers were washed with water
6. dry with materialbrine, dried over anhydrous MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customto afford a gum