Water → 1-(4-Fluorophenyl)-2-(4-pyridyl)vinyl 4-fluorobenzoate

HRID 2376713

Reaction equation

HRID 2376713 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.O>CN(C=O)C>[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([O:18][C:10]([C:7]2[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=2)=[CH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 678794-Fluorobenzoyl chlorideHCID 103308811-(4-Fluorophenyl)-2-(pyridin-4-yl)ethan-1-one

Product 1

HCID 684458621-(4-Fluorophenyl)-2-(4-pyridyl)vinyl 4-fluorobenzoateYield 152.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (0.81 g, 18.6 mmol) in DMF (30 mL) under argon atmosphere and cooled to 0° C., a solution of 1-(4-fluorophenyl)-2-(4-pyridyl)ethanone (2.00 g, 9.3 mmol, obtained in reference example 1) in DMF (15 mL) was added and stirred to room temperature for 30 minutes. It was then cooled to 0° C. and a solution of 4-fluorobenzoyl chloride (2.95 g, 1.9 mmol) in DMF (10 mL) was added. It was stirred at room temperature overnight. Water was added and the solvent was evaporated off. The residue was dissolved in a mixture of CHCl3 and water and the phases were separated. The aqueous phase was extracted with CHCl3 (×3). The organic phase was washed with water (×2), dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 0.98 g of the desired compound as a yellow solid (yield: 31%).

Workup

  1. temperatureIt was then cooled to 0° C.
  2. stirringIt was stirred at room temperature overnight
  3. customthe solvent was evaporated off
  4. dissolutionThe residue was dissolved in a mixture of CHCl3 and water
  5. customthe phases were separated
  6. extractionThe aqueous phase was extracted with CHCl3 (×3)
  7. washThe organic phase was washed with water (×2)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated to dryness
  10. customThe crude product obtained
  11. customwas purified by chromatography on silica gel
  12. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-bf14e2f31c04463c8fe140e44843f792
Source dataset
uspto-grants-2008_12
Patent number
US07468376B2

Linked notes

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