4'-Fluoroacetophenone → 2-(4-Fluorophenyl)-2-methyloxirane

HRID 1401419Notes

Reaction equation

HRID 1401419 reaction equation
[I-].[CH3:2][S+](C)C.[H-].[Na+].[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1>CS(C)=O.O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([CH3:2])[CH2:16][O:17]2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 98284'-FluoroacetophenoneHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 178694862-(4-Fluorophenyl)-2-methyloxirane

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a solution of trimethylsulfonium iodide (1-1.2 equiv.) in DMSO is added sodium hydride 50%-55% dispersion in oil (1-1.8 equiv.) portionwise over 5 min. and stirred for 1 h at RT. A solution of 1-(4-fluorophenyl)ethanone (1 equiv.) in DMSO is added to the reaction mixture dropwise over 20 min. and stirred at RT for 4 h. The reaction is monitored by TLC and at completion the reaction mixture is poured in water (100 mL) and extracted with EtOAc. The combined organic extract is washed with water, followed by brine, dried over sodium sulfate and evaporated to dryness.

Workup

  1. stirringstirred at RT for 4 h
  2. extractionextracted with EtOAc
  3. extractionThe combined organic extract
  4. washis washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-20015d98d4174363965b69a19870afd2
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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