Dimethylformamide → Propanenitrile, 2-methyl-2-(methylsulfonyl)-

反応式

[CH3:1][S:2]([CH2:5][C:6]#N)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].I[CH3:15].C[N:17]([CH:19]=O)C>>[CH3:15][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])([CH3:6])[C:19]#[N:17]

参加物

反応物 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 75283(Methylsulfonyl)acetonitrile

生成物 1

HCID 3014848Propanenitrile, 2-methyl-2-(methylsulfonyl)-収率 78%

実験手順

To a solution of 2-(methylsulfonyl)acetonitrile (60 g, 504 mmol) in DMF (252 mL) at 0° C. was added potassium carbonate (209 g, 1511 mmol) portion-wise, followed by iodomethane (136 mL, 1511 mmol). After 15 minutes, the ice bath was removed and the reaction was stirred at RT for 48 hours. The reaction mixture was filtered through a Celite pad, and the filter cake was rinsed with ethyl acetate and ether. The combined filtrates were concentrated and partitioned between ether and water. The organic portion was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the titled intermediate (58 g, 78% yield) as an off-white solid.