tert-butyl 5-(hydroxymethyl)-1H-indole-1-carboxylate → tert-Butyl 5-formyl-1H-indole-1-carboxylate

HRID 2297993Notes

Reaction equation

HRID 2297993 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][OH:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[Mn+2]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]=[O:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 21865484tert-butyl 5-(hydroxymethyl)-1H-indole-1-carboxylate

Product 1

HCID 11172622tert-Butyl 5-formyl-1H-indole-1-carboxylateYield 98.5%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butoxycarbonylindol-5-yl methanol (2.56 g, 10.35 mmol) in dry methylene chloride (60 mL) was added manganese oxide (9 g, 103.5 mmol). The reaction mixture was stirred for 3 h at room temperature and then heated at reflux. After 3 h, the heterogeneous slurry was filtered through Celite and concentrated to afford N-tert-butoxycarbonyl-5-formylindole (2.5 g).

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. waitAfter 3 h
  4. filtrationthe heterogeneous slurry was filtered through Celite
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-97bd27c8b64f4a688eb833b19f88197e
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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