Trimethylsulfonium iodide → 2-tert-Butyl-2-(3-phenoxypropyl)oxirane

HRID 1649623Notes

Reaction equation

HRID 1649623 reaction equation
[CH3:1][C:2]([CH3:16])([C:4](=[O:15])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:3].[I-].[CH3:18][S+](C)C>O1CCCC1>[CH3:3][C:2]([C:4]1([CH2:5][CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:18][O:15]1)([CH3:16])[CH3:1]

Participants

4

Reactant 2

HCID 75127Trimethylsulfonium iodideHCID 14076005HCID 14076005, compound

Product 1

HCID 140760082-tert-Butyl-2-(3-phenoxypropyl)oxiraneYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9 g (41 mMol) of 2,2-dimethyl-6-phenoxy-hexan-3-one are added dropwise to a mixture of 5.5 g (49 mMol) of potassium tert.-butylate in 40 ml of tetrahydrofuran at room temperature, with stirring, whereupon a clear yellowish solution forms. 12.5 g (61.5 mMol) of trimethylsulphonium iodide are then added and the mixture is stirred at 20° to 25° C. for 12 hours. Thereafter, the reaction mixture is filtered and the filtrate is concentrated under reduced pressure. The residue which remains is taken up in methylene chloride and the resulting solution is washed three times with water. After the organic phase has been dried, the solvent is stripped off. 7.8 g (81% of theory) of 2-(1,1-dimethyl-ethyl)-2-(3-phenoxypropyl)-oxirane are obtained in this manner in the form of a liquid of refractive index nD20 =1.503. ##STR13##

Workup

  1. stirringthe mixture is stirred at 20° to 25° C. for 12 hours
  2. filtrationThereafter, the reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. washthe resulting solution is washed three times with water
  5. customAfter the organic phase has been dried

Sources & evidence

ORD record
ord-52414ab9ff7e44d991e53980e3f41227
Source dataset
uspto-grants-1990_05
Patent number
US04921529

Reaction notes

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