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

HRID 2212745Notes

Reaction equation

HRID 2212745 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-811a318e0ae44c5b887f172c1ae436bb
Source dataset
uspto-grants-2006_09
Patent number
US07101875B2

Reaction notes

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