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

HRID 42554

反応式

HRID 42554 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-40e9414b27794d87b43015f35338f418
出典データセット
uspto-grants-2013_09
特許番号
US08536194B2

関連ノート

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