Methanol → (1H-indol-2-yl)methanol

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:16](O)=[O:17].CO>C1COCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[CH2:16][OH:17]

Participants

Procedure

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).