(5-Fluoro-6-methoxypyridin-3-yl)methanol → 5-Fluoro-6-methoxypyridine-3-carbaldehyde

HRID 385564Notes

Reaction equation

HRID 385564 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][OH:11])[CH:5]=[N:6][C:7]=1[O:8][CH3:9]>ClCCl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[C:7]([O:8][CH3:9])=[N:6][CH:5]=[C:4]([CH:3]=1)[CH:10]=[O:11]

Participants

4

Procedure

To a solution of 0.54 g of (5-fluoro-6-methoxypyridin-3-yl)methanol in 5 mL of dichloromethane, 1.5 g of manganese dioxide was added. The mixture was stirred at room temperature for 3 hours, thereto were then added 0.89 g of manganese dioxide and 4 mL of dichloromethane, and the mixture was stirred for 1 hour. Thereto were further added 1.5 g of manganese dioxide and 2 mL of dichloromethane, and the mixture was stirred at room temperature for 2 hours 30 minutes. After leaving overnight, the insoluble substance was filtered off, and the filtration residue was washed with chloroform. The solvent was distilled off under reduced pressure to obtain 0.48 g of 5-fluoro-6-methoxynicotinaldehyde as a yellow solid.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. stirringthe mixture was stirred at room temperature for 2 hours 30 minutes
  3. customAfter leaving overnight
  4. filtrationthe insoluble substance was filtered off
  5. washthe filtration residue was washed with chloroform
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-56330486ba3a4994a1b974a44941248d
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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