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

HRID 1045534Notes

Reaction equation

HRID 1045534 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

The title compound was prepared by following general procedure 3. To a solution of trimethylsulfonium iodide (3.5 g, 17.15 mmol, 1.2 equiv.) in DMSO (30 mL) was added sodium hydride 50%-55% dispersion in oil (0.97 g, 22.2mmol, 1.5 equiv.) portionwise over 5 min. and stirred for 1 h at RT. A solution of 1-(4-fluorophenyl) ethanone (2 g, 14.47 mmol, 1 equiv.) in DMSO (10 mL) was added to the reaction mixture dropwise over 20 min. and stirred at RT for 4 h. The progress of the reaction was checked by TLC and the reaction mixture was poured in 100 mL water and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with water (2×150 mL), followed by brine. The organic layer was dried over sodium sulfate and evaporated to dryness to yield a brown oil (2.2 g). 1H NMR (d6-acetone) was consistent with the structure. Product Rf 0.8 (ethyl acetate: hexane 10:90)

Workup

  1. stirringstirred at RT for 4 h
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic extracts were washed with water (2×150 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-630193972edf4a6d89e04130da00271e
Source dataset
uspto-grants-2013_10
Patent number
US08569287B2

Reaction notes

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