(1H-indol-5-yl)methanol → Indole-5-carboxaldehyde

HRID 2120236Notes

Reaction equation

HRID 2120236 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][OH:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1>ClCCl.[O-2].[Mn+2]>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 1

HCID 2773458(1H-indol-5-yl)methanol

Product 1

HCID 589040Indole-5-carboxaldehydeYield 40.1%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (1H-indol-5-yl)-methanol (3.8 g, 25.8 mmol) and manganese oxide (5 g, 57.5 mmol) in dichloromethane (50 mL) was stirred at room temperature for 60 hours. After the usual work-up and chromatography, 1.5 g (40%) of 1H-indole-5-carbaldehyde was obtained.

Sources & evidence

ORD record
ord-2db05878f6b749a4a39e3243b99b03a5
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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