反应详情

温度

0 °C

To a solution of 1-benzyl-1H-indole-3-carbaldehyde O-allyl-oxime (2.965 g, 10.2 mmol) in tetrahydrofuran (50 mL) cooled to 0° C. was added 9-BBN (0.5 M in THF)(50.0 mL, 25.0 mmol). The reaction was stirred at 0° C. for 1 hour and then warmed to room temperature over 30 minutes. Hydrogen peroxide (12 mL) was carefully added followed by a 10% NaOH solution (20 mL) and stirring continued at room temperature for 25 minutes. The reaction was quenched by the addition of saturated sodium bisulfite and extracted with ethyl acetate. The combined organic were washed with saturated sodium bisulfite and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography through silica gel using ethyl acetate/hexanes (10/90 to 40/60) to give 1-benzyl-1H-indole-3-carbaldehyde O-(3-hydroxy-propyl)-oxime (1.298 g, 41%) as a white solid. mp=76.4-77.7° C.; mass spectrum (+ES, M+H) m/z 309. 1H NMR (400 MHz, CDCl3); δ 8.33 (s, 1H), 8.01 (d, 1H), 7.92 (s, 1H), 7.49 (d, 1H), 7.22 (m, 7H), 5.44 (s, 2H), 4.47 (t, 1H), 4.13 (t, 2H), 3.52 (q, 2H), 1.82 (m, 2H). Elemental analysis: Calcd. for C19H20N2O2: C, 74.0; H, 6.54; N, 9.08. Found: C, 73.74; H, 6.46; N, 8.95.

1. temperaturewarmed to room temperature over 30 minutes
2. stirringstirring
3. waitcontinued at room temperature for 25 minutes
4. customThe reaction was quenched by the addition of saturated sodium bisulfite
5. extractionextracted with ethyl acetate
6. washThe combined organic were washed with saturated sodium bisulfite and brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated in vacuo
9. customThe residue was purified by flash chromatography through silica gel