反应详情

LiAlH4 (1.0 m in THF, 5.0 mL, 5.0 mmol) was slowly added to a solution of indole-2-carboxylic acid (403 mg, 2.5 mmol) in dry THF (18 mL) at 0° C. The resultant yellow solution was warmed to room temperature and stirred for 18 hours. MeOH (0.5 mL) was added and the solution concentrated under reduced pressure (3×). The resultant orange syrup was partially dissolved in CHCl3 (150 mL) and washed consecutively with H2O (10 mL) and NH4Cl (10 mL). The aqueous layer was extracted with CHCl3 (2×25 mL). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. Purification by column chromatography on silica gel (100% CH2Cl2) afforded the desired alcohol (250 mg, 68%) as a yellow solid. 1H NMR (CDCl3) δ 4.84 (s, 2H), 6.42 (d, 1H, J=0.9 Hz), 7.11–7.20 (m, 2H), 7.36 (d, 1H, J=7.5 Hz), 7.59 (d, 1H, J=7.5 Hz), 8.31 (br s, 1H).

1. concentrationthe solution concentrated under reduced pressure (3×)
2. dissolutionThe resultant orange syrup was partially dissolved in CHCl3 (150 mL)
3. washwashed consecutively with H2O (10 mL) and NH4Cl (10 mL)
4. extractionThe aqueous layer was extracted with CHCl3 (2×25 mL)
5. dry with materialThe combined organic extracts were dried (MgSO4)
6. concentrationconcentrated under reduced pressure
7. customPurification by column chromatography on silica gel (100% CH2Cl2)