6-Hydroxymethylindole → 1H-Indole-6-carboxaldehyde

HRID 2236429Notes

Reaction equation

HRID 2236429 reaction equation
[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>ClCCl.[O-2].[Mn+4].[O-2]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 1

HCID 27734596-Hydroxymethylindole

Product 1

HCID 27734351H-Indole-6-carboxaldehydeYield 80.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a dissolved solution of (1H-Indol-6-yl)-methanol (100 mg, 0.68 mmole) in dichloromethane (31 ml), manganese (IV) oxide (1.9 g, 21.9 mmol) is added. The reaction mixture stirred at room temperature for 8 hours and then passed through celite. The reaction mixture is then concentrated to give a yellow oil (80 mg, 0.55 mmole). MS (ESI) m/z 146.2 (M+1).

Workup

  1. concentrationThe reaction mixture is then concentrated

Sources & evidence

ORD record
ord-15eac74b038242aab5f1f02f1344eb7b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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