Methyl iodide → HCID 12819456, compound

HRID 1660460Notes

Reaction equation

HRID 1660460 reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][O:15]2)[CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[H][H].[CH3:32]I.[Cl-].[NH4+]>CS(C)=O>[CH3:1][S:2][C:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][O:15]2)[CH:9]=1)([CH3:32])[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86737871HCID 86737871, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12819456HCID 12819456, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl α-methylthio[m-(5,5-dimethyl-2-phenyl-1,3-dioxa-2-cyclohexyl)phenyl]acetate (406 mg) was dissolved in 3 ml of anhydrous dimethyl sulfoxide. Sodium hydride (50 mg; 65% content) was added, and the mixture was stirred for 15 minutes at room temperature. The mixture turned into a reddish brown solution with the evolution of hydrogen. When 0.15 ml of methyl iodide was added to the solution, its color vanished. The mixture was stirred for an additional 10 minutes at room temperature. An aqueous solution of ammonium chloride (0.2 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 and concentrated under reduced pressure. The residue was chromatographed on a column of Florisil using benzene and diethyl ether as eluents to afford 368 mg of methyl α-methylthio-α-[m-(5,5-dimethyl-2-phenyl-1,3-dioxa-2-cyclohexyl)phenyl]propionate as a colorless oily substance in a yield of 87%.

Workup

  1. stirringThe mixture was stirred for an additional 10 minutes at room temperature
  2. extractionthe mixture was extracted three times with 20 ml of diethyl ether
  3. washThe organic layer was washed twice with 10 ml of water
  4. dry with materialdried over anhydrous sodium
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on a column of Florisil

Sources & evidence

ORD record
ord-04f562f677b04c2aa60dd20691893c21
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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