Methoxide → (E)-3-(5-methyl-2-nitrophenyl)-2-(6-methylpyridin-3-yl)acrylonitrile

Participants

Reaction Conditions

Reaction Steps

Sodium metal (1.9 g, 0.0848 mol) was dissolved in MeOH (180 mL), and the resulting methoxide solution was cooled to 0° C. To this was added 2-(6-methylpyridin-3-yl)acetonitrile (11.19 g, 0.0848 mol), and the reaction mixture was stirred for 30 min. at 0° C. 5-Methyl-2-nitrobenzaldehyde (7.0 g, 0.0424 mol) was added at 0° C., and the mixture was further stirred for 1 h at 0° C. After completion of reaction (monitored by TLC), the mixture was diluted with water (100 mL), and extracted with EtOAc (3×150 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by column chromatography (20% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch) to give the desired compound as a yellow colored solid (6.5 g, 59% yield).

Provenance & Evidence