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

HRID 1821478Notes

Reaction equation

HRID 1821478 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-8a8b7275bd8e4209b416e77b78dc86af
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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