Methyl morpholine oxide → 5-Fluoro-2-methyl-3-pyridinecarboxaldehyde

HRID 1510671Notes

Reaction equation

HRID 1510671 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[C:5]([CH3:8])=[N:6][CH:7]=1.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[C:4]([CH:3]=1)[CH:9]=[O:10]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 57815512959616-50-3

Product 1

HCID 552651665-Fluoro-2-methyl-3-pyridinecarboxaldehydeYield 63.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 32 mg of (5-fluoro-2-methylpyridin-3-yl)methanol in 2 mL of dichloromethane, 80 mg of molecular sieves 3A and 40 mg of 4-methylmorpholine N-oxide were added, and the mixture was stirred at room temperature for 30 minutes. Thereto was added 6.0 mg of tetrapropyl ammonium perruthenate, and the mixture was stirred at room temperature for 1 hour 30 minutes. The insoluble substance was filtered off, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=100:1 to obtain 20 mg of 5-fluoro-2-methylnicotinaldehyde as a colorless oily substance.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour 30 minutes
  2. filtrationThe insoluble substance was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7a04b66dc33b43f58afe1882e92af8f8
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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