Sodium hydride → 2-(2-Phenylpropyl)-2-trifluoromethyl-oxiran

HRID 1266432Notes

Reaction equation

HRID 1266432 reaction equation
O[C:2]([C:24]([F:27])([F:26])[F:25])([CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])[CH2:3][O:4]S(C1C=CC(C)=CC=1)(=O)=O.[H-].[Na+]>CN(C)C=O.O>[C:18]1([CH:16]([CH3:17])[CH2:15][C:2]2([C:24]([F:27])([F:26])[F:25])[CH2:3][O:4]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 185511734-Toluenesulfonic acid-(2-hydroxy-4-phenyl-2-trifluoromethyl-pentyl)-ester

Product 1

HCID 185512062-(2-Phenylpropyl)-2-trifluoromethyl-oxiranYield 87.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

400 mg of 4-toluenesulfonic acid-(2-hydroxy-4-phenyl-2-trifluoromethyl-pentyl)ester in 5 ml of dimethylformamide is mixed at 0° C. with 35 mg of sodium hydride (80% in mineral oil). After one hour at 0° C., it is diluted with water and extracted with dichloromethane. The dichloromethane phase is washed with water, dried (Na2SO4) and concentrated by evaporation. The residue is distilled. 200 mg of 2-(2-phenylpropyl)-2-trifluoromethyl-oxiran, boiling point 110° C./1 hPa, is obtained.

Workup

  1. extractionextracted with dichloromethane
  2. washThe dichloromethane phase is washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation
  5. distillationThe residue is distilled

Sources & evidence

ORD record
ord-6724421a6dd94ea382dc5c4dcd1c7f24
Source dataset
uspto-grants-2003_04
Patent number
US06548534B2

Reaction notes

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