Methyl iodide → HCID 12917658, compound

HRID 1660474Notes

Reaction equation

HRID 1660474 reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:22][CH3:23])([O:20][CH3:21])[C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH3:26]I.[Cl-].[NH4+]>CS(C)=O>[CH3:1][S:2][C:3]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:22][CH3:23])([O:20][CH3:21])[C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:9]=1)([CH3:26])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 12917657HCID 12917657, compound

Product 1

HCID 12917658HCID 12917658, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl α-methylthio[p-[dimethoxy(2-thienyl)methyl]phenyl]acetate (457 mg) was dissolved in 3 ml of anhydrous dimethyl sulfoxide, and 60 mg (65% content) of sodium hydride was added. The mixture was stirred at room temperature for 30 minutes. Then, 0.15 ml of methyl iodide was added, and the mixture was stirred at room temperature for 20 minutes. After adding an aqueous solution of ammonium chloride (0.5 g/30 ml), the mixture was extracted three times with 20 ml of methylene chloride. The extract was washed twice with 10 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a Florisil column using benzene as an eluent to give 443 mg of methyl α-methylthio-α-[p-[dimethoxy(2-thienyl)methyl]phenyl]propionate as a colorless oil in a yield of 93%.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 minutes
  2. extractionthe mixture was extracted three times with 20 ml of methylene chloride
  3. washThe extract was washed twice with 10 ml of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on a Florisil column

Sources & evidence

ORD record
ord-4a0abc3f530b476dac02c658deb328f9
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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