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Sodium hydride → 1-[4-[[2-(Cyclooctyloxy)ethyl]thio]phenyl]ethanone

HRID 2225765
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HRID 2225765 반응식
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:18][CH2:19][O:20][CH:21]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)(=O)=O>CN(C)C=O.O>[CH:21]1([O:20][CH2:19][CH2:18][S:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1
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참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 47131801-(4-Sulfanylphenyl)ethan-1-oneHCID 190043182-(Cyclooctyloxy)ethyl methanesulfonate

생성물 1

HCID 190044781-[4-[[2-(Cyclooctyloxy)ethyl]thio]phenyl]ethanone수율 70.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228
Dimethylformamide
용매

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온도
60 °C

실험 절차

A stirred mixture of 1-(4-mercaptophenyl)ethanone (0.76 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.218 g), stirred for 20 minutes and treated with 2-(cyclooctyloxy)ethyl methanesulfonate (1.25 g). The mixture was heated at 60° C. overnight, cooled, diluted with water, extracted twice with dichloromethane, and the organic layers were washed with water. The combined organic layers were dried (Na2SO4), filtered, and evaporated to give crude material which was purified by HPLC (dichloromethane-hexane-ethyl acetate; 48:48:4) to provide 1.08 g of 1-[4-[[2-(cyclooctyloxy)ethyl]thio]phenyl]ethanone as a colorless oil.

후처리

  1. temperaturecooled
  2. extractionextracted twice with dichloromethane
  3. washthe organic layers were washed with water
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude material which
  8. customwas purified by HPLC (dichloromethane-hexane-ethyl acetate; 48:48:4)

출처 및 근거

ORD 기록
ord-beef348d17884277a7a676c30781b88a
출처 데이터셋
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05344843

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