Sodium borohydride → 1H-Indole-4-methanol, 1-ethyl-

HRID 1055409Notes

Reaction equation

HRID 1055409 reaction equation
[BH4-].[Na+].[CH2:3]([N:5]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([CH:14]=[O:15])[C:8]=2[CH:7]=[CH:6]1)[CH3:4]>CCO.C(Cl)Cl>[CH2:3]([N:5]1[C:13]2[C:8](=[C:9]([CH2:14][OH:15])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 172211551-ethyl-1H-indole-4-carbaldehyde

Product 1

HCID 287420511H-Indole-4-methanol, 1-ethyl-Yield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

NaBH4 (49.8 mg, 1.32 mmol, Eq: 0.3) was added to a solution of 1-ethyl-1H-indole-4-carbaldehyde (800 mg, 4.39 mmol, Eq: 1.00) in EtOH (30 mL) and DCM (15 mL) at 0° C. and the mixture was warmed to RT and stirred overnight. The mixture concentrated to remove DCM and the resulting mixture diluted with NH4Cl, extracted with DCM and concentrated. The residue was purified by silica gel chromatography to give the title compound (700 mg, 91%) as a yellow oil.

Workup

  1. concentrationThe mixture concentrated
  2. customto remove DCM
  3. additionthe resulting mixture diluted with NH4Cl
  4. extractionextracted with DCM
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-256705504abe4c56926b0ec9de4bb094
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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