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

HRID 510020Notes

Reaction equation

HRID 510020 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:10]=[O:11].N1C2C(=CC=CC=2)C=C1C(OCC)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>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

5

Reactant 3

HCID 73125Ethyl indole-2-carboxylateHCID 96389Indole-2-carboxaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 98783(1H-indol-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1H-indole-2-carbaldehyde derivatives (1) may be prepared by reduction of commercially available or well known ethyl 1H-indole-2-carboxylate derivatives (12) with a reducing agent such as LAH in an aprotic solvent such as THF to give the corresponding (1H-indol-2-yl)methanol derivative (13). Oxidation with an oxidizing agent such as active manganese dioxide in an aprotic solvent such as DCM gives the desired 1H-indole-2-carbaldehyde derivatives (1).

Sources & evidence

ORD record
ord-151c42a5dc8442b592135c83a737b998
Source dataset
uspto-grants-2015_08
Patent number
US09096595B2

Reaction notes

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