(5-Methylpyridin-3-yl)methanol → 5-Methylpyridine-3-carbaldehyde

HRID 1186418Notes

Reaction equation

HRID 1186418 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH3:9])[CH:8]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH3:9])[CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 11962777(5-Methylpyridin-3-yl)methanol

Product 1

HCID 141411585-Methylpyridine-3-carbaldehydeYield 98%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

3-Hydroxymethyl-5-methylpyridine (972 mg, 7.89 mmol) was dissolved in dichloromethane (30 mL). To this, manganese dioxide (7.5 g) was added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered through Celite and the solvent was evaporated off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=19/1) to give 3-formyl-5-methylpyridine (936 mg, yield: 98%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was evaporated off under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform/methanol=19/1)

Sources & evidence

ORD record
ord-ee53202e5774433595cd37df97cf0cb7
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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