Dimethylformamide → 2-Fluoro-4-(pyridin-2-ylmethoxy)benzaldehyde

HRID 1694028Notes

Reaction equation

HRID 1694028 reaction equation
CN(C)C=O.[F:6][C:7]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].[H-].[Na+].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24]Cl>O>[F:6][C:7]1[CH:14]=[C:13]([O:15][CH2:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=2)[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 23393Picolyl chlorideHCID 24758Sodium hydrideHCID 5872462-Fluoro-4-hydroxybenzaldehyde

Product 1

HCID 592553212-Fluoro-4-(pyridin-2-ylmethoxy)benzaldehydeYield 40.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an N,N-dimethylformamide (10.0 mL) solution of 2-fluoro-4-hydroxy-benzaldehyde (1.60 g, 11.4 mmol) was added sodium hydride (547 mg, 13.7 mmol, 60% in oil) under nitrogen atmosphere at 0° C., which was stirred for 30 minutes at room temperature. 2-Picolyl chloride (2.80 g, 17.1 mmol) was then added at room temperature and stirred for 1 hour at 70° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:3) to obtain the title compound (1.07 g, 40.6%).

Workup

  1. stirringstirred for 1 hour at 70° C
  2. extractionwhich was then extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:3)

Sources & evidence

ORD record
ord-62fd2bed02a1462da78236118fd3c2ab
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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