反应详情

温度

-45 °C

To a solution of compound 5 (1.0 g, 3.24 mmol) in dry THF (70 mL) was added n-BuLi (2.5 M, 2 mL) dropwise at −78° C. over 30 minutes. The reaction was stirred at −45° C. for 30 minutes. Then a solution of iodine in THF (20 mL) was dropwise added at −78° C. over 10 minutes. The resulting mixture was stirred at 0° C. for 2 hours. The reaction was quenched with saturated aqueous Na2S2O3 solution (10 mL). Then the reaction mixture was diluted with EtOAc (200 mL), and washed with brine (50 mL×2). The separated organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluted by PE/EtOAc=10:1 to 2:1) to afford compound 6 (930 mg, 66% yield) as a white solid. LC-MS: m/z 435.99 [M+1]+. 1H NMR (400 MHz, CDCl3): δ 7.89 (s, 1H), 7.37˜7.26 (m, 5H), 3.82 (d, J=12.4 Hz, 1H), 3.59 (d, J=12.4 Hz, 1H), 3.42˜3.38 (m, 1H), 2.98 (d, J=8.4 Hz, 1H), 2.82˜2.81 (m, 1H), 2.55˜2.51 (m, 1H), 2.45˜2.42 (m, 1H), 1.96˜1.92 (m, 1H), 1.22 (d, J=7.2 Hz, 3H).

1. stirringThe resulting mixture was stirred at 0° C. for 2 hours
2. customThe reaction was quenched with saturated aqueous Na2S2O3 solution (10 mL)
3. additionThen the reaction mixture was diluted with EtOAc (200 mL)
4. washwashed with brine (50 mL×2)
5. dry with materialThe separated organic phase was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by column chromatography on silica gel (eluted by PE/EtOAc=10:1 to 2:1)