Dimethyl Sulfoxide → 2-Ethyl-2-(4-fluorophenyl)oxirane

HRID 1400362노트

반응식

HRID 1400362 반응식
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:22])[CH2:20][CH3:21])=[CH:15][CH:14]=1>C1COCC1>[CH2:20]([C:19]1([C:16]2[CH:15]=[CH:14][C:13]([F:12])=[CH:18][CH:17]=2)[CH2:8][O:22]1)[CH3:21]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 680044-FluoropropiophenoneHCID 75127Trimethylsulfonium iodide

생성물 1

HCID 594552622-Ethyl-2-(4-fluorophenyl)oxirane

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
65 °C

실험 절차

DMSO is added to NaH (1-1.8 equiv.) and heated to 65° C. for 1 h. THF is added at the same temperature and heated for another 10 min. After 10 min., the reaction mixture is cooled to 0° C. Trimethylsulfonium iodide (1-1.2 equiv.) is added and the contents stirred for 10 min. after which the solution of 1-(4-fluorophenyl)propan-1-one (1 equiv.) in THF is added dropwise. After complete addition, the reaction mixture is stirred at RT for 2 h; the reaction is monitored by LCMS. After completion, the reaction mixture is poured in ice water, extracted in diethyl ether, dried over sodium sulfate and concentrated at 25° C. to get the crude product.

후처리

  1. temperatureheated for another 10 min
  2. temperaturethe reaction mixture is cooled to 0° C
  3. additionis added dropwise
  4. additionAfter complete addition
  5. extractionextracted in diethyl ether
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated at 25° C.

출처 및 근거

ORD 기록
ord-51a79bd48f7c462395beb3f6bf381130
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906925B2

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