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

HRID 1506144

Reaction equation

HRID 1506144 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

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%).

Workup

  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))

Sources & evidence

ORD record
ord-f886d7f436004bc58563b288f1ce0f26
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Linked notes

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