Methyl iodide → Methyl alpha-methylthio-alpha-(m-phenoxyphenyl)propionate
Reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH3:23]I.[Cl-].[NH4+]>CN(C)C=O>[CH3:1][S:2][C:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)([CH3:23])[C:4]([O:6][CH3:7])=[O:5]Participants
Procedure
Methyl α-methylthio(m-phenoxyphenyl)acetate (1.963 g) was dissolved in anhydrous dimethylformamide, and under ice cooling, 280 mg (65% content) of sodium hydride was added. The mixture was stirred for 10 minutes. Then, 0.60 ml of methyl iodide was added, and the mixture was stirred under ice cooling for 5 minutes and then at room temperature for 30 minutes. After adding an aqueous solution of ammonium chloride (500 mg/40 ml), the reaction mixture was extracted three times with 20 ml of diethyl ether. The organic layer 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 silica gel column using hexane and benzene as eluents to afford 1.930 g of methyl α-methylthio-α-(m-phenoxyphenyl)propionate as an oil in a yield of 94%. Distillation of this substance gave a fraction boiling at 147°-149° C./0.08 mmHg.
Workup
- stirringthe mixture was stirred under ice cooling for 5 minutes
- waitat room temperature for 30 minutes
- extractionthe reaction mixture was extracted three times with 20 ml of diethyl ether
- washThe organic layer was washed three times with 10 ml of water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was chromatographed on a silica gel column
Sources & evidence
- ORD record
- ord-3593426b84354911a822642d5c807fb0
- Source dataset
- uspto-grants-1981_07
- Patent number
- US04278802
Reaction notes
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