Methyl iodide → HCID 12917670, compound

HRID 1733644Notes

Reaction equation

HRID 1733644 reaction equation
[CH3:1][S:2][CH:3]([C:8]1[S:9][C:10]([C:13]([O:22][CH3:23])([O:20][CH3:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=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[S:9][C:10]([C:13]([O:20][CH3:21])([O:22][CH3:23])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)([CH3:26])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 20556692HCID 20556692, compound

Product 1

HCID 12917670HCID 12917670, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl α-methylthio[5-(α,α-dimethoxybenzyl)-2-thienyl]acetate (1.162 g) was dissolved in 6 ml of anhydrous dimethyl sulfoxide, and 150 mg (65% content) of sodium hydride was added. The mixture was stirred at room temperature for 30 minutes. Methyl iodide (0.30 ml) was added, and the mixture was stirred at room temperature for 15 minutes. 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 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 column of Florisil using benzene as an eluent to afford 932 mg of methyl α-methylthio-α-[5-(α,α-dimethoxybenzyl)-2-thienyl]propionate in a yield of 77% as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 minutes
  2. extractionthe mixture was extracted three times with 20 ml of diethyl ether
  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 column of Florisil

Sources & evidence

ORD record
ord-e44dbb41c10d41f5ac084c71b0d64b90
Source dataset
uspto-grants-1980_12
Patent number
US04242519

Reaction notes

Loading…