Cornforth reagent → 7-(Benzyloxy)-1H-indole-4-carbaldehyde

HRID 1198545Notes

Reaction equation

HRID 1198545 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH2:22]([O:29][C:30]1[C:38]2[NH:37][CH:36]=[CH:35][C:34]=2[C:33]([CH2:39][OH:40])=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[CH2:22]([O:29][C:30]1[C:38]2[NH:37][CH:36]=[CH:35][C:34]=2[C:33]([CH:39]=[O:40])=[CH:32][CH:31]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 19102610HCID 19102610, compound

Product 1

HCID 132434867-(Benzyloxy)-1H-indole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid pyridinium dichromate (5.4 g., 15.5 mmol) was added in portions over 8 hours to a stirred solution of 7-benzyloxyindole-4-methanol (1.17 g, 4.6 mmol) in dichloromethane (30 ml). The dark mixture was stirred for a further 2 hours, filtered through a bed of silica and evaporated.

Workup

  1. filtrationfiltered through a bed of silica
  2. customevaporated

Sources & evidence

ORD record
ord-b8cab2e3ccfd4c7ab7f395631ee0a405
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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