Water → 2-[4-(Trifluoromethyl)phenyl]oxirane

HRID 1506144

반응식

HRID 1506144 반응식
[I-].C[S+](C)C.[H-].[Na+].[F:8][C:9]([F:19])([F:18])[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[CH2:15])=[CH:12][CH:11]=1.[OH2:20]>CS(C)=O>[F:8][C:9]([F:18])([F:19])[C:10]1[CH:17]=[CH:16][C:13]([CH:14]2[CH2:15][O:20]2)=[CH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 27827981-Ethenyl-4-(trifluoromethyl)benzene

생성물 1

HCID 99900162-[4-(Trifluoromethyl)phenyl]oxirane수율 81%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

Trimethylsulfonium iodide (4.08 g, 20.0 mmol) in dimethyl sulfoxide (15 mL) was stirred with sodium hydride (55 wt % dispersion in mineral oil, 873 mg, 20.0 mmol) at room temperature for 1 hour and then with 4-(trifluoromethyl)styrene (2.96 g, 17.0 mmol) in dimethyl sulfoxide (10 mL) at room temperature for 2 hours. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 (v/v)) to give the title compound as a colorless oil (2.59 g, yield 81%).

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 (v/v))

출처 및 근거

ORD 기록
ord-f886d7f436004bc58563b288f1ce0f26
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216999B2

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