(1H-indol-2-yl)methanol → Indole-2-carboxaldehyde

HRID 537852Notes

Reaction equation

HRID 537852 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][OH:11].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCCCCC>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:10]=[O:11]

Participants

5

Reactant 2

HCID 98783(1H-indol-2-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 96389Indole-2-carboxaldehydeYield 29%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirred solution of crude (1H-indol-2-yl)methanol 17 (5.37 g, 36.53 mmol) in anhydrous CH2Cl2 (50 mL) at cold-bath temperature (˜10° C.) was added portionwise pyridinium chlorochromate (PCC) (9.44 g, 40.18 mmol). Reaction was stirred at ambient temperature for 2 hours. Reaction was diluted with CH2Cl2 and filtered through a pad of celite and washed with CH2Cl2. After evaporation of solvent, crude product was silica-column chromatographed (Biotage) using Acetone:Hexane as an eluent to yield 1H-indole-2-carbaldehyde 18 (1.52 g, 29% yield).

Workup

  1. customReaction
  2. customReaction
  3. filtrationfiltered through a pad of celite
  4. washwashed with CH2Cl2
  5. customAfter evaporation of solvent, crude product
  6. customchromatographed (Biotage)

Sources & evidence

ORD record
ord-adaa6b8313ce47fc90c4d5863d438cbb
Source dataset
uspto-grants-2014_10
Patent number
US08865709B2

Reaction notes

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