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

HRID 2376713

반응식

HRID 2376713 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bf14e2f31c04463c8fe140e44843f792
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07468376B2

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