n-Benzyl-2-hydroxymethyl-4-methoxyindole → n-Benzyl-4-methoxyindole-2-carboxaldehyde

HRID 567377Notes

Reaction equation

HRID 567377 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([O:17][CH3:18])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:19][OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([O:17][CH3:18])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:19]=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22741392n-Benzyl-2-hydroxymethyl-4-methoxyindole

Product 1

HCID 22739184n-Benzyl-4-methoxyindole-2-carboxaldehydeYield 113.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.2 g of N-benzyl-2-hydroxymethyl-4-methoxyindole (12 mmol) and 15 g of manganese dioxide (172 mmol) in 50 cc of dry dichloromethane was heated at reflux for 6 hours, cooled down to r.t. and filtered through celite. Concentration to dryness afford 3.6 g of a yellow solid. mp.130-31° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. filtrationfiltered through celite
  4. concentrationConcentration to dryness

Sources & evidence

ORD record
ord-8ae54035c3c34f60809a3f2c45e4a3e2
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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