Cornforth reagent → Indole-7-carboxaldehyde

HRID 54525

Reaction equation

HRID 54525 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[CH2:31][OH:32])[CH:24]=[CH:23]1>ClCCl>[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[CH:31]=[O:32])[CH:24]=[CH:23]1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 2773460(1H-indol-7-yl)methanol

Product 1

HCID 2734629Indole-7-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid pyridinium dichromate (1.77 g, 5.1 mmol) is added in portions over 3 hours to a stirred solution of 7-indolemethanol (0.5 g, 3.4 mmol) in dichloromethane (50 ml). The mixture is stirred for a further 2 hours then filtered through a pad of Celite filter aid. The filtrate is evaporated and the residue purified by chromatography on silica in ethyl acetate-hexane (1:3)

Workup

  1. filtrationthen filtered through a pad of Celite
  2. filtrationfilter aid
  3. customThe filtrate is evaporated
  4. customthe residue purified by chromatography on silica in ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-4cd06d0fdd3140dc9e0b2b96b9a110a2
Source dataset
uspto-grants-1997_04
Patent number
US05622969

Linked notes

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