Water → 2-(2-Phenylethyl)oxirane

HRID 442506

Reaction equation

HRID 442506 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 (48.4 g.) 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-b912e908b32f491b9473384849b9421a
Source dataset
uspto-grants-1977_08
Patent number
US04045568

Linked notes

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