Methyl iodide → Methyl 3-(1-methyl-1H-imidazol-4-yl)prop-2-enoate

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Reaction Steps

NaH (0.85 g of a 60% dispersion in oil, 21.2 mmol) was placed in a flask, suspended in hexanes, and allowed to settle. The hexanes was decanted and DMF (50 mL) was added, followed by 35-2 (2 g, 10.6 mmol). After 10 minutes methyl iodide (0.79 mL, 12.7 mmol) was added. After stirring for 24 hr the solution was diluted with EtOAc and H2O and the layers were separated. The water layer was basified to pH 11 with saturated NaHCO3 and extracted with EtOAc and CH2Cl2. The organic layers were combined and evaporated. The residue was chromatographed (5% CH3OH/CHCl3 saturated with NH3) to give 35-3 as a white solid.

Provenance & Evidence