Methyl iodide → HCID 18649180, compound

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Reaction Steps

A solution of 2',4'-difluoro-2-(3-pyridyl)acetophenone oxime in 25 ml of dimethoxyethane is treated in portions with 0.50 g of sodium hydride dispersion (55% in oil) and the mixture is stirred at room temperature for 30 minutes. 1.8 g of methyl iodide is then added and the mixture is heated to reflux temperature. After 4 hours, it is cooled to room temperature, poured onto ice and extracted with ethyl acetate, and the organic phase is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. After separation by column chromatography on silica gel, (E)-2',4'-difluoro-2-(3-pyridyl)acetophenone O-methyloxime [1H-NMR (CDCl3, 200 MHz): 4.05 ppm (s, CH3O--N=)] is obtained first and then (Z)-2',4'-difluoro-2-(3-pyridyl)acetophenone O-methyloxime [1H-NMR (CDCl3, 200 MHz): 3.91 ppm (s, CH3O--N=)].

Provenance & Evidence