Indole-2-carboxylic acid → (1H-indol-2-yl)methanol

HRID 899627Notes

Reaction equation

HRID 899627 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10](O)=[O:11].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:11][CH2:10][C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

4

Reactant 2

HCID 72899Indole-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 98783(1H-indol-2-yl)methanolYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of indole-2-carboxylic acid (485 mg, 3.01 mmol) in THF (20 mL), cooled to 0° C. under nitrogen, was added a suspension of LiAlH4 (248 mg, 6.2 mmol) in THF (6 mL). The resultant green suspension was stirred at room temperature for 4 hours. The reaction was quenched by slow addition of an 80% aqueous MeOH solution (1.0 mL) and the solvent was evaporated under reduced pressure. The residue was suspended in MeOH and filtered through Celite, rinsing with MeOH. Concentration of the filtrate under reduced pressure gave a yellow oil. Purification by flash column chromatography on silica (MeOH/CH2Cl2, 19:1 then 9:1) gave the alcohol as a beige solid (357 mg, 2.43 mmol, 81%). 1H NMR (CDCl3) δ 1.85 (t, 1H, J=6.0 Hz), 4.83 (d, 2H, J=6.0 Hz), 6.42 (d, 1H, J=1.5 Hz), 7.11 (td, 1H, J=6.9, 1.5 Hz), 7.20 (td, 1H, J=6.9, 1.5 Hz), 7.35 (dd, 1H, J=6.9, 1.5 Hz), 7.59 (d, 1H, J=6.9 Hz), 8.33 (br s., 1H).

Workup

  1. additionwas added
  2. customThe reaction was quenched by slow addition of an 80% aqueous MeOH solution (1.0 mL)
  3. customthe solvent was evaporated under reduced pressure
  4. filtrationfiltered through Celite
  5. washrinsing with MeOH
  6. customConcentration of the filtrate under reduced pressure gave a yellow oil
  7. customPurification by flash column chromatography on silica (MeOH/CH2Cl2, 19:1

Sources & evidence

ORD record
ord-59d638a6420e4e6aa184ec55fd6d712c
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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