Sodium Hydroxide → 1-((2-Oxiranyl)methoxy)-2-(4,4,5,5,5-pentafluoropentylthio)ethane

HRID 1792358노트

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HRID 1792358 반응식
[OH-].[Na+].[CH2:3]1[O:5][C@@H:4]1[CH2:6]Cl.[F:8][C:9]([F:21])([C:17]([F:20])([F:19])[F:18])[CH2:10][CH2:11][CH2:12][S:13][CH2:14][CH2:15][OH:16]>S([O-])(O)(=O)=O.C([NH3+])(C)(C)C>[O:5]1[CH2:3][CH:4]1[CH2:6][O:16][CH2:15][CH2:14][S:13][CH2:12][CH2:11][CH2:10][C:9]([F:21])([F:8])[C:17]([F:18])([F:19])[F:20]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 149428(+)-EpichlorohydrinHCID 22033252HCID 22033252, 화합물

생성물 1

HCID 220332271-((2-Oxiranyl)methoxy)-2-(4,4,5,5,5-pentafluoropentylthio)ethane수율 63%

시약·촉매·용매 1

HCID 24996679t-Butylammonium hydrogen sulfate촉매

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온도
0 °C

실험 절차

A mixture of 50% acqueous NaOH (1.85 ml), S-epichlorohydrin (1.142 g, 12.34 mmole) and t-butylammonium hydrogen sulfate (24 mg) was vigorously stirred at 0° C., for half an hour and allowed to reach room temperature. To this mixture was added 2-(4,4,5,5,5-pentafluoropentylthio)ethan-1-ol (735 mg, 3.08 mmole) at room temperature. The reaction mixture was stirred for 18 hours and quenched with water. The aqueous phase was extracted with ethyl acetate. Then, the organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to flash chromatography on silica gel (n-hexane:ethyl acetate=7:1) to give the title compound (568 mg, yield 63%) as a colorless oil.

후처리

  1. customto reach room temperature
  2. stirringThe reaction mixture was stirred for 18 hours
  3. customquenched with water
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washThen, the organic layer was washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-bc2e03d9f3304b1c8aa18d08880755d0
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074819B2

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