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

HRID 2225765
ノート
印刷プレビュー

反応式

HRID 2225765 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228
Dimethylformamide
溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-beef348d17884277a7a676c30781b88a
出典データセット
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05344843

反応ノート

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