Water → 2-(2-Phenylethyl)oxirane

HRID 463277Notes

Reaction equation

HRID 463277 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 J. Am. Chem. Soc., 84, 867 (1962) and ibid., 87, 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. extractionThe, extract
  3. washwas washed with water (2×150 ml.)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-0b13738d680e4bfdbd39195780c8c5e7
Source dataset
uspto-grants-1985_05
Patent number
US04518607

Reaction notes

Loading…