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

HRID 603941Notes

Reaction equation

HRID 603941 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-7345d29a27ee46439184948ee701acef
Source dataset
uspto-grants-2011_03
Patent number
US07906548B2

Reaction notes

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