(4-Methoxy-5-methylpyridin-2-yl)methanol → 4-Methoxy-5-methylpyridine-2-carbaldehyde

HRID 385581Notes

Reaction equation

HRID 385581 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10][OH:11])[CH:4]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH:10]=[O:11])[CH:4]=1

Participants

4

Reactant 1

HCID 15163463(4-Methoxy-5-methylpyridin-2-yl)methanol

Product 1

HCID 578154004-Methoxy-5-methylpyridine-2-carbaldehydeYield 60%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.13 g of (4-methoxy-5-methylpyridin-2-yl)methanol in 2 mL of dichloromethane, 0.14 g of manganese dioxide was added. The mixture was stirred for 6 hours while dividedly further adding 0.36 g of manganese dioxide at room temperature. The insoluble substance was filtered off, the solvent was distilled off under reduced pressure, and the resultant residue was purified by flash column chromatography using gradient elution of hexane:ethyl acetate=9:1 to 4:1 to obtain 77 mg of 4-methoxy-5-methylpyridine-2-carbaldehyde as a white solid.

Workup

  1. filtrationThe insoluble substance was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe resultant residue was purified by flash column chromatography
  4. washelution of hexane

Sources & evidence

ORD record
ord-d76f08b895f14d208f921bbd8fbacdc2
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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