Dimethylformamide → 4-(Pyridin-3-yloxy)benzaldehyde

HRID 1693966Notes

Reaction equation

HRID 1693966 reaction equation
CN(C)C=O.[OH:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.F[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 46774194-(Pyridin-3-yloxy)benzaldehydeYield 27.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To an N,N-dimethylformamide (30.0 mL) solution of 3-hydroxypyridine (3.00 g, 31.5 mmol) and 4-fluorobenzaldehyde (5.08 g, 41.0 mmol) was added potassium carbonate (8.71 g, 63.0 mmol) under nitrogen atmosphere, which was stirred for 17 hours at 70° C. The reaction mixture was then cooled to room temperature and water was added thereto, followed by extraction 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=1:1→3:1) to obtain the title compound (1.70 g, 27.1%).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionfollowed by extraction 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=1:1→3:1)

Sources & evidence

ORD record
ord-b30cc48828ed43bf8bcd9cb4b6a18373
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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