反应详情

温度

0 °C

To a solution of 62.8 (94 mg, 0.15 mmol) in THF (1.5 mL) were added 30% H2O2 (0.17 mL, 1.50 mmol) and 1N LiOH (0.73 mL, 0.73 mmol) at 0° C. The mixture was stirred for 1 hour at 0° C., adjusted to pH 3 with aqueous HCl, and extracted with EtOAc. The combined organics were washed with 1N Na2SO3 (pH 3) and brine, dried (Na2SO4), and concentrated. The residue was dissolved in 9:1 MeCN/DMF (1.5 mL), and to the solution were added K2CO3 (30 mg, 0.22 mmol) and iodomethane (20 μL, 0.22 mmol). The mixture was stirred overnight at room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and concentrated. The crude product was chromatographed on silica gel (0-40% EtOAc/hexane) to afford 62.9 (64 mg, 88%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.28 (d, 1H), 7.65 (d, 2H), 7.60 (d, 2H), 7.20 (d, 2H), 7.15 (s, 1H), 6.95 (d, 2H), 6.08 (d, 1H), 5.10 (s, 2H), 4.59 (t, 1H), 3.64 (s, 3H), 3.31 (dd, 1H), 2.95 (dd, 1H), 2.28 (s, 3H).

1. extractionextracted with EtOAc
2. washThe combined organics were washed with 1N Na2SO3 (pH 3) and brine
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in 9:1 MeCN/DMF (1.5 mL)
6. stirringThe mixture was stirred overnight at room temperature
7. washwashed with water and brine
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated
10. customThe crude product was chromatographed on silica gel (0-40% EtOAc/hexane)