(6-Chloro-1H-indol-2-yl)methanol → 6-Chloro-1H-indole-2-carbaldehyde

HRID 988888Notes

Reaction equation

HRID 988888 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:11][OH:12])[NH:8]2)=[CH:4][CH:3]=1>C1COCC1.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH:11]=[O:12])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 16115151(6-Chloro-1H-indol-2-yl)methanol

Product 1

HCID 161151526-Chloro-1H-indole-2-carbaldehydeYield 62%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To (6-chloro-1H-indol-2-yl)-methanol (37.7 mmol) in THF at 0° C. was added manganese (IV) oxide and the mixture was stirred at rt for 16 h. The mixture was filtered over celite and rinsed with THF and EtOAc and evaporated to near dryness. The solid was filtered and washed with cold EtOAc/hex to give 6-Chloro-1H-indole-2-carbaldehyde (62%, 2 steps).

Workup

  1. filtrationThe mixture was filtered over celite
  2. washrinsed with THF and EtOAc
  3. customevaporated
  4. filtrationThe solid was filtered
  5. washwashed with cold EtOAc/hex

Sources & evidence

ORD record
ord-0d84e619ee4d4ffabe98932e9fbfc6b7
Source dataset
uspto-grants-2003_10
Patent number
US06635771B2

Reaction notes

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