Methyl iodide → HCID 12917661, compound

HRID 1732452Notes

Reaction equation

HRID 1732452 reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:10][CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[H][H].[CH3:22]I.[Cl-].[NH4+]>CN(C)C=O>[CH2:14]([C:11]1[CH:10]=[CH:9][C:8]([C:3]([S:2][CH3:1])([CH3:22])[C:4]([O:6][CH3:7])=[O:5])=[CH:13][CH:12]=1)[CH:15]([CH3:17])[CH3:16]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 12819447HCID 12819447, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 12917661HCID 12917661, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl α-methylthio(p-isobutylphenyl)acetate (471 mg) was dissolved in 5 ml of anhydrous dimethylformamide, and with stirring under ice cooling, 75 mg (65% content) of sodium hydride was added. Hydrogen evolved immediately. When the mixture was stirred for about 10 minutes, the generation of hydrogen subsided. Methyl iodide (0.25 ml) was added, and the mixture was stirred under ice cooling for 30 minutes, and then at room temperature for 40 minutes. Then, an aqueous solution of ammonium chloride (0.5 g/30 ml) was added, and the mixture was extracted three times with 20 ml of diethyl ether. The organic layer was washed twice with 10 ml of water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using hexane/benzene as an eluant to afford 422 mg of methyl α-(p-isobutylphenyl)-α-(methylthio)propionate as a colorless oil in a yield of 85%.

Workup

  1. stirringWhen the mixture was stirred for about 10 minutes
  2. stirringthe mixture was stirred under ice cooling for 30 minutes
  3. extractionthe mixture was extracted three times with 20 ml of diethyl ether
  4. washThe organic layer was washed twice with 10 ml of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-0ef5c076d9204fffac9328de789e1ad7
Source dataset
uspto-grants-1980_12
Patent number
US04237298

Reaction notes

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