Water → 2-Fluoroethyl p-Toluenesulfonate

HRID 339559

반응식

HRID 339559 반응식
[F:1][CH2:2][CH2:3][OH:4].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1.O.CCOC(C)=O>N1C=CC=CC=1>[F:1][CH2:2][CH2:3][O:4][S:11]([C:8]1[CH:9]=[CH:10][C:5]([CH3:15])=[CH:6][CH:7]=1)(=[O:13])=[O:12]

참가 물질

6

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 97372-Fluoroethanol

생성물 1

HCID 2560192-Fluoroethyl p-Toluenesulfonate수율 78%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 2-fluoroethanol (1.92 g, 29.97 mmol) in dry pyridine (15 ml) under an atmosphere of argon at 0° C. was added p-toluenesulphonyl chloride over 15 min, maintaining the temperature below 5° C. The reaction mixture was then stirred at 0° C. for 4 h, then at room temperature for 12 h. The reaction mixture was cooled to 0° C. and ice (15 g) was added followed by water (40 ml) and EtOAc (50 ml). The organic extract was washed with water (30 ml), 1 M HCl (until aqueous extracts were acidic), 10% sodium carbonate (2×30 ml), brine (40 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give the title compound (5.10 g, 78%) as a colourless oil.

후처리

  1. temperaturemaintaining the temperature below 5° C
  2. waitat room temperature for 12 h
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. extractionThe organic extract
  5. washwas washed with water (30 ml), 1 M HCl (until aqueous extracts were acidic), 10% sodium carbonate (2×30 ml), brine (40 ml)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-3b1adff8ea8a40a198aa5711e8a6cac8
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895313B2

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