反应详情

温度

40 °C

To a mixture of [(9-benzyl-7-methoxy-9H-carbazol-4-yl)oxy]acetonitrile (0.9 g, 2.6 mmol) in dry THF (50 mL) is added borane-methylsulfide complex (0.75 mL, 7.9 mmol). The mixture is heated at 40° C. overnight. Methanol is slowly added to mixture until addition of methanol did not evolve gas. The solvents are removed under reduced pressure. Methanol (50 mL) is added to the residue then removed under reduced pressure. Methanol (100 mL) and concentrated hydrochloric acid (3 mL) is added to the residue. The mixture is heated at 75° C. for 2.5 h. The mixture is neutralized with saturated potassium carbonate and partitioned between water and ethyl acetate. The layers are separated and the organic layer washed twice with brine. The organic layer is dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography, silica gel (100 mL) using CH2Cl2: CH3OH (95:5) as eluent gave 0.52 g (58%) of the title compound; 1H NMR (DMSO-d6) δ2.48, 3.8, 4.12, 5.59, 6.69, 6.8, 7.14, 7.2, 8.03; Anal. Calcd for C22H22N2O2: C, 76.28; H, 6.40; N, 8.09. Found: C, 76.00; H, 6.54; N, 7.92.

1. additionis added borane-methylsulfide complex (0.75 mL, 7.9 mmol)
2. customThe solvents are removed under reduced pressure
3. additionMethanol (50 mL) is added to the residue
4. customthen removed under reduced pressure
5. additionMethanol (100 mL) and concentrated hydrochloric acid (3 mL) is added to the residue
6. temperatureThe mixture is heated at 75° C. for 2.5 h
7. custompartitioned between water and ethyl acetate
8. customThe layers are separated
9. washthe organic layer washed twice with brine
10. dry with materialThe organic layer is dried over anhydrous sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated