反应详情

温度

0 °C

To a stirred solution of 24 (1.30 g, 2.72 mmol) in anhydrous MeOH (15 mL) at room temperature under nitrogen were added NiCl2×6H2O (605 mg, 2.54 mmol) and NaBH4 (192 mg, 5.08 mmol), respectively. The reaction mixture was stirred for 50 min, concentrated, cooled to 0° C., treated with HCl (10 mL, 1M) followed by addition of NH4OH (29%) (pH 9-10), and finally extracted with AcOEt. The organic extract was successively washed with water and brine, dried over Na2SO4, filtered, and concentrated to afford the title compound 25 (450 mg, 85% yield) as a yellow solid. NMR (400 MHz, CDCl3) δ(ppm): 9.04 (t, J=5.6 Hz, 1H), 8.73 (s, 1H), 8.23 (s, 1H), 7.07 (t, J=8.8 Hz, 1H), 6.48 (dd, J=2.4 and 13.2 Hz, 1H), 6.40 (dd, J=2.4 and 8.8 Hz, 1H), 5.47 (s, 2H), 3.62-3.52 (m, 4H), 3.44 (q, J=6.8 Hz, 2H), 2.56-2.48 (m, 2H), 2.46-2.40 (m, 4H).

1. concentrationconcentrated
2. additiontreated with HCl (10 mL, 1M)
3. additionfollowed by addition of NH4OH (29%) (pH 9-10)
4. extractionfinally extracted with AcOEt
5. extractionThe organic extract
6. washwas successively washed with water and brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated