Dimethyl Sulfoxide → oxirane, 2-methyl-2-phenyl-

HRID 1481397Notes

Reaction equation

HRID 1481397 reaction equation
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])[CH3:13]>C1COCC1>[CH3:13][C:12]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:8][O:14]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7410AcetophenoneHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 16398oxirane, 2-methyl-2-phenyl-

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 acetophenone (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-837a4a138db74f9e898a5f670908bb15
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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