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Sodium hydride → 2,2,2-Trifluoro-1-(4-fluorophenyl)ethyl trifluoromethanesulfonate

HRID 17011
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HRID 17011 반응식
[H-].[Na+].[F:3][C:4]([F:15])([F:14])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[OH:6].[F:16][C:17]([F:23])([F:22])[S:18](Cl)(=[O:20])=[O:19]>C(OCC)C>[F:15][C:4]([F:3])([F:14])[CH:5]([O:6][S:18]([C:17]([F:23])([F:22])[F:16])(=[O:20])=[O:19])[C:7]1[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=1
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 79000Trifluoromethanesulfonyl chlorideHCID 111482462,2,2-Trifluoro-1-(4-fluorophenyl)ethanol

생성물 1

HCID 575620972,2,2-Trifluoro-1-(4-fluorophenyl)ethyl trifluoromethanesulfonate수율 74.9%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A dried 50 mL of flask was charged sodium hydride, 60% dispersion in mineral oil (624 mg, 15.6 mmol) under N2 and then washed with dried hexane (20 mL) twice. Dried ethyl ether (10 mL) was added and a solution of 2,2,2-trifluoro-1(RS)-(4-fluorophenyl)ethanol (90% ee) (2.5 g, 12.89 mmol) in ethyl ether (10 mL) was added at 0° C. After completion of addition, the reaction mixture was allowed to warm up to room temperature and stirred for 1 h. A solution of trifluoromethanesulfonyl chloride (3.28 g, 19.5 mmol) in ethyl ether (10 mL) was added at 0° C. After completion of addition, the reaction was allowed to warm up to room temperature and stirred for 1 h. The solvent was removed under rot-vap and diluted with hexane (150 mL) and washed with a saturated NaHCO3 n and brine. After drying with MgSO4, the organic solvent was removed to give trifluor-methanesulfonic acid 2,2,2-trifluoro-1(RS)-(4-fluorophenyl)ethyl ester (3.15 g) (90% ee) as a colorless oil which was used in the next step without further purification.

후처리

  1. washwashed with dried hexane (20 mL) twice
  2. additionDried ethyl ether (10 mL) was added
  3. additionAfter completion of addition
  4. additionAfter completion of addition
  5. temperatureto warm up to room temperature
  6. stirringstirred for 1 h
  7. customThe solvent was removed under rot-vap
  8. additiondiluted with hexane (150 mL)
  9. washwashed with a saturated NaHCO3 n and brine
  10. dry with materialAfter drying with MgSO4
  11. customthe organic solvent was removed

출처 및 근거

ORD 기록
ord-8f39b88f41da4254a6a7667099ca1295
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737300B2

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