Diethyl Ether → 2-(3-Methoxyphenyl)-2-methyloxirane

HRID 894918Notes

Reaction equation

HRID 894918 reaction equation
[CH3:1]S(C)(=O)=C.CO[CH:8](OC)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].C[CH2:20][O:21]CC>CS(C)=O.O>[CH3:20][O:21][C:15]1[CH:16]=[C:11]([CH:12]=[CH:13][CH:14]=1)[C:9]1([CH3:8])[O:10][CH2:1]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 2483332,2-Dimethoxy-1-phenylethanoneHCID 6396768Dimethylsulfoxonium methylide

Product 1

HCID 204969162-(3-Methoxyphenyl)-2-methyloxirane

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of dimethylsulfoxonium methylide (69.4 mmoles) in dimethyl sulfoxide (65 ml.) at room temperature is added solid 3-l -dimethoxyacetophenone (8.33 g., 55.5 mmoles). The reaction mixture is stirred for one hour at 25° C., for one-half hour at 50° C. and is then cooled. The mixture is diluted with water (50 ml.) and added to a mixture of ice water (200 ml.)--ether (250 ml.)--low boiling petroleum ether (25 ml.). The organic extract is washed twice with water (250 ml.), dried (MgSO4) and evaporated to an oil which is fractionally distilled.

Workup

  1. temperatureis then cooled
  2. extractionThe organic extract
  3. washis washed twice with water (250 ml.)
  4. dry with materialdried (MgSO4)
  5. customevaporated to an oil which
  6. distillationis fractionally distilled

Sources & evidence

ORD record
ord-23b5d1020e8f4ab59f87e7356365424b
Source dataset
uspto-grants-1981_08
Patent number
US04284829

Reaction notes

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