Methyl iodide → Methyl alpha-methylthio-alpha-[m-(2phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate

HRID 1660459Notes

Reaction equation

HRID 1660459 reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:18][CH2:17][CH2:16][O:15]2)[CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[H][H].[CH3:29]I.[Cl-].[NH4+]>CS(C)=O.O>[CH3:1][S:2][C:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:18][CH2:17][CH2:16][O:15]2)[CH:9]=1)([CH3:29])[C:4]([O:6][CH3:7])=[O:5]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86737870Methyl alpha-methylthio[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 12819455Methyl alpha-methylthio-alpha-[m-(2phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionateYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

Methyl α-methylthio[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]acetate (6.88 g) was dissolved in 30 ml of anhydrous dimethyl sulfoxide. While cooling at 15° C., 810 mg (65% content) of sodium hydride was added, and the mixture was stirred for 1 hour. Hydrogen evolved gradually to form a reddish brown solution. While cooling at 15° C., 1.5 ml of methyl iodide was added to this solution, whereupon the color vanished immediately. After stirring for 5 minutes, an aqueous solution of ammonium chloride (2 g/10 ml) was added, and then 40 ml of water was added. The mixture was extracted first with 50 ml of diethyl ether, and then three times with 10 ml of diethyl ether. The extract was washed three times with 10 ml of water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a column of Florisil using benzene and diethyl ether as eluents to afford 6.14 g of methyl α-methylthio-α-[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate as a colorless oil in a yield of 86%.

Workup

  1. customto form a reddish brown solution
  2. temperatureWhile cooling at 15° C.
  3. stirringAfter stirring for 5 minutes
  4. extractionThe mixture was extracted first with 50 ml of diethyl ether
  5. washThe extract was washed three times with 10 ml of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed on a column of Florisil

Sources & evidence

ORD record
ord-e96591db1c2943638829f7659a667307
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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