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Water → 1-[2-(p-Toluenesulfonyloxy)ethyl]-2,3,6-trifluorobenzene

HRID 2107605
ノート
印刷プレビュー

反応式

HRID 2107605 の反応式
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][CH2:11][OH:12].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C.O>C(Cl)Cl>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O:12][CH2:11][CH2:10][C:3]2[C:4]([F:9])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])(=[O:21])=[O:20])=[CH:15][CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 148346752-(2,3,6-Trifluorophenyl)ethan-1-ol

生成物 1

HCID 156318391-[2-(p-Toluenesulfonyloxy)ethyl]-2,3,6-trifluorobenzene収率 120.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

To a solution of 2-(2,3,6-trifluorophenyl)ethyl alcohol (1.5 g) in methylene chloride (10 ml) are added with stirring p-toluenesulfonyl chloride (2.2 g) and triethylamine (2.0 ml), and the mixture is stirred at room temperature for 5 hours. The reaction mixture is poured into water and is extracted with diethyl ether. The ether layer is washed with aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride and dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (solvent, methylene chloride) and recrystallized from diethyl ether-n-hexane to give 1-[2-(p-toluenesulfonyloxy)ethyl]-2,3,6-trifluorobenzene (3.4 g), as colorless prisms, m.p. 73°-74° C.

後処理

  1. extractionis extracted with diethyl ether
  2. washThe ether layer is washed with aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (solvent, methylene chloride)
  6. customrecrystallized from diethyl ether-n-hexane

出典と根拠

ORDレコード
ord-a0d1f57ebeca49d2969caf7c6d0a4e43
出典データセット
uspto-grants-1990_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04935420

反応ノート

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