Water → 2-Hydroxy-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl 4-methylbenzenesulfonate

HRID 623477ノート

反応式

HRID 623477 の反応式
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]([OH:14])[CH2:12][OH:13])=[CH:7][CH:6]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.N1C=CC=CC=1.O>ClCCl>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:13][CH2:12][CH:11]([OH:14])[C:8]2[CH:9]=[N:10][C:5]([O:4][CH2:3][C:2]([F:1])([F:15])[F:16])=[CH:6][CH:7]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chloride2 回HCID 675099191-(6-(2,2,2-Trifluoroethoxy)pyridin-3-yl)ethane-1,2-diol

生成物 1

HCID 874265272-Hydroxy-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl 4-methylbenzenesulfonate収率 99%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethane-1,2-diol (1.01 g, 4.24 mmol, Step-3, single enantiomer), p-toluenesulfonyl chloride (0.97 g, 5.09 mmol) and pyridine (3.43 mL, 42.4 mmol) in dichloromethane (21 mL) is stirred at room temperature for 20 hours. Then p-toluenesulfonyl chloride (0.97 g, 5.09 mmol) is added to the reaction mixture and stirred for 24 hours. The reaction mixture is poured into water and extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1 to 1:1) to give 1.64 g (99% yield) of the title compound as colorless oil.

後処理

  1. stirringstirred for 24 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1 to 1:1)

出典と根拠

ORDレコード
ord-61a3584e0640493f88955f8f6e0168da
出典データセット
uspto-grants-2016_04
特許番号
US09302991B2

反応ノート

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