1H-indole-6-carboxylic acid → 6-Hydroxymethylindole

HRID 2236428Notes

Reaction equation

HRID 2236428 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10](O)=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][OH:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 5952301H-indole-6-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 27734596-HydroxymethylindoleYield 3.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-indole carboxylic acid (5 g, 31.05 mmol) in tetrahydrofuran (310 ml) is added lithium aluminum hydride (5.89 mg, 155.2 mmol) at 0° C. The reaction mixture is refluxed for 6 hours. The resulting mixture is then quenched with 5% potassium hydrogen sulfate (100 ml) and extracted with ether (100 mL). The organic layer is then dried with sodium sulfate and concentrated to give a white solid (156 mg) MS (ESI) m/z 148.8 (M+1).

Workup

  1. temperatureThe reaction mixture is refluxed for 6 hours
  2. customThe resulting mixture is then quenched with 5% potassium hydrogen sulfate (100 ml)
  3. extractionextracted with ether (100 mL)
  4. dry with materialThe organic layer is then dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5be3a4e60a534140b09873af85eaad44
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…