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Sodium hydride → 2',4'-dichloro-2-(3-pyridyl)acetophenone O-[2-(4-fluorophenoxy)ethyl]oxime

HRID 1681308
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HRID 1681308 반응식
[H-].[Na+].[F:3][C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10]Br)=[CH:6][CH:5]=1.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[C:22](=[N:30][OH:31])[CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1>CN(C)C=O>[F:3][C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][O:31][N:30]=[C:22]([C:16]2[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=2[Cl:14])[CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:6][CH:5]=1
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 20641711-(2-Bromoethoxy)-4-fluorobenzeneHCID 71415949N-[1-(2,4-Dichlorophenyl)-2-(pyridin-3-yl)ethylidene]hydroxylamine

생성물 1

HCID 540012232',4'-dichloro-2-(3-pyridyl)acetophenone O-[2-(4-fluorophenoxy)ethyl]oxime

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

0.55 g of sodium hydride dispersion (50% in oil) and then 2.20 g of 2-(4-fluorophenoxy)ethyl bromide are added with stirring to a solution of 2.81 g of 2',4'-dichloro-2-(3-pyridyl)acetophenone oxime in 20 ml of dimethylformamide. The reaction mixture is heated to 100° C. and stirred at this temperature for 1 hour. It is then cooled to room temperature and poured onto ice. The aqueous mixture is extracted with methylene chloride, and the organic phase is washed twice with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. After chromatography on silica gel using n-hexane/ethyl acetate (7:3) as the eluent, 2',4'-dichloro-2-(3-pyridyl)acetophenone O-[2-(4-fluorophenoxy)ethyl]oxime is obtained as an E/Z isomer mixture in the form of a slightly yellow oil.

후처리

  1. temperatureIt is then cooled to room temperature
  2. additionpoured onto ice
  3. extractionThe aqueous mixture is extracted with methylene chloride
  4. washthe organic phase is washed twice with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-bec53edc2e6d43508b3515a95325c476
출처 데이터셋
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05171354

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