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

HRID 1045553Notes

Reaction equation

HRID 1045553 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

The title compound was prepared by following general procedure 3. DMSO was added to NaH (1 equiv.) and heated to 65° C. for 1 h. THF was added at the same temperature and heated for another 10 min. After 10 min., the reaction mixture was cooled to 0° C. Trimethylsulfonium iodide (1 equiv.) was added and stirred for 10 min. after which the solution of 1-(4-fluorophenyl) propan-1-one (1 equiv.) in THF was added dropwise. After complete addition, the reaction mixture was stirred at RT for 2 h. The product was detected by LCMS and the reaction mixture was poured into ice water, extracted in diethyl ether (4×50 mL), dried over Na2SO4 and concentrated at 25° C. to obtain the product.

Workup

  1. temperatureheated for another 10 min
  2. temperaturethe reaction mixture was cooled to 0° C
  3. additionwas added dropwise
  4. additionAfter complete addition
  5. extractionextracted in diethyl ether (4×50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated at 25° C.
  8. customto obtain the product

Sources & evidence

ORD record
ord-52e8e2b03f644d13a405bdd20d43e215
Source dataset
uspto-grants-2013_10
Patent number
US08569287B2

Reaction notes

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