Ethyl indole-2-carboxylate → (1H-indol-2-yl)methanol

HRID 1038417Notes

Reaction equation

HRID 1038417 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](OCC)=[O:11].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 73125Ethyl indole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 98783(1H-indol-2-yl)methanolYield 106.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To ethyl 1H-indole-2-carboxylate 16 (6.5 g, 34.35 mmol) in THF at 0° C. was added lithium aluminum hydride solution (1M, in THF 1.43 g, 37.78 mmol) dropwise and the reaction mixture was stirred for 3.5 hours at 0° C. The reaction mixture was quenched with H2O, 15% NaOH, and H2O before it was filtered and rinsed with THF. Reaction mixture was dried (anhydrous Na2SO4) and evaporation of the solvent gave 5.37 g (100% yield) of the crude (1H-indol-2-yl)methanol 17 which was used directly in the next step.

Workup

  1. customThe reaction mixture was quenched with H2O, 15% NaOH, and H2O before it
  2. filtrationwas filtered
  3. washrinsed with THF
  4. customReaction mixture
  5. customwas dried
  6. custom(anhydrous Na2SO4) and evaporation of the solvent

Sources & evidence

ORD record
ord-74363f693c9a4e20a670746570adc871
Source dataset
uspto-grants-2013_10
Patent number
US08551992B2

Reaction notes

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