Water → 2-(Methylthio)-1-[4-(trifluoromethyl)phenyl]-1-propanone

HRID 1885893Notes

Reaction equation

HRID 1885893 reaction equation
[CH3:1][S:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)=[O:5].[H-].[Na+].[CH3:18]I.O>O1CCCC1>[CH3:1][S:2][CH:3]([CH3:18])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:8][CH:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10633422HCID 10633422, compound

Product 1

HCID 198784282-(Methylthio)-1-[4-(trifluoromethyl)phenyl]-1-propanoneYield 40.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5.00 g of 2-methylthio-4'-(trifluoromethyl)acetophenone dissolved in 50 ml of tetrahydrofuran was added under ice-cooling 0.855 g of a 60% aqueous solution of sodium hydride, and the mixture was reacted at room temperature with stirring until no bubbles were produced. After an addition of 3.34 g of methyl iodide, the mixture was stirred at room temperature for a further 2 hours. The resultant reaction mixture was poured into ice-cooled water and extracted with dichloromethane. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the residue was purified by silica gel column chromatography- using n-hexane to obtain 2.16 g of an oily product of 2-methylthio-4'-(trifluoromethyl)propiophenone (yield: 40.8%).

Workup

  1. additionwas added under ice-
  2. customthe mixture was reacted at room temperature
  3. customwere produced
  4. stirringthe mixture was stirred at room temperature for a further 2 hours
  5. customThe resultant reaction mixture
  6. additionwas poured into ice-
  7. extractionextracted with dichloromethane
  8. washThe organic layer was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customAfter evaporation of the solvent
  11. customthe residue was purified by silica gel column

Sources & evidence

ORD record
ord-56d7102f052745eb985a11303740b3e1
Source dataset
uspto-grants-1992_09
Patent number
US05147886

Reaction notes

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