Water → 2-(2-Phenylethyl)oxirane

HRID 1678983Notes

Reaction equation

HRID 1678983 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].[CH3:12][S+](C)(C)=O.[H-].[Na+].O>CS(C)=O>[O:10]1[CH:9]([CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 7707BenzenepropanalHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)

Product 1

HCID 1359552-(2-Phenylethyl)oxirane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Phenylpropionaldehyde (26.8 g.) is added under nitrogen to the ylide prepared from trimethylsulfoxonium iodide (48.4g.) and sodium hydride (55% dispersion in oil; 9.6 g.) in dry dimethylsulfoxide (200 ml.), according to the procedure in Journal of the American Chemical Society, Vol. 84, page 867 (1962) and Vol. 87, page 1353 (1965). After one hour, the solution was poured into 1 liter of water and the product extracted with ether (3 × 300 ml.). The extract was washed with water (2 × 150 ml.) dried (MgSO4) and evaporated to give an oil, 1,2-epoxy-4-phenylbutane, used directly in the next step.

Workup

  1. extractionthe product extracted with ether (3 × 300 ml.)
  2. washThe extract was washed with water (2 × 150 ml.)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-638da426aefa48ca8052fbf8f6b2373d
Source dataset
uspto-grants-1978_03
Patent number
US04078071

Reaction notes

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