[CH3:1][S:2][CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)[C:4]#[N:5].[CH3:20][O-].[Na+].CI.[Cl-].[NH4+]>CO>[CH3:1][S:2][C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)([CH3:20])[C:4]#[N:5]
433 mg of alpha-(methylthio)(m-benzoylphenyl)-acetonitrile was dissolved in 2 ml of anhydrous methanol. The solution was stirred in an atmosphere of argon under ice cooling. Then, 0.65 ml of a 2.5 M methanol solution of sodium methoxide was added, and then 0.15 ml of methyl iodide was added dropwise. Under ice cooling, the mixture was stirred for 1 hour, and an aqueous solution of ammonium chloride (0.5 g/30 ml) was added. The mixture was extracted with 20 ml of methylene chloride three times. The extract was washed with 10 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; methylene chloride) to afford 334 mg (yield 73%) of alpha-(methylthio)-alpha-(m-benzoylphenyl)-propionitrile as a pale yellow oil.
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