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

HRID 623477노트

반응식

HRID 623477 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chloride2회HCID 675099191-(6-(2,2,2-Trifluoroethoxy)pyridin-3-yl)ethane-1,2-diol

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-61a3584e0640493f88955f8f6e0168da
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302991B2

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