Sodium hydride → HCID 23047285, compound

Participants

Reaction Conditions

Reaction Steps

1-Cyano-1-(4-chlorophenyl)-2-(3-pyridyl)ethane (4.0 gms, 0.0165 m) was placed in a 100 ml three neck flask, under a nitrogen atmosphere, equipped with a magnetic stirrer, thermometer, gas inlet tube and a cooling bath. To the flask was added 50 ml DMF-toluene (1:2), and the resulting solution was cooled to 5° C. Sodium hydride (0.4 gm, 0.018m of 60% NaH) was added and the mixture was stirred for 30 minutes. Then 4-methoxyphenyl-p-toluene-sulfonate (5.0 gm, 0.0165 m) was added and the mixture was stirred for 1 hour at 5° C., followed by stirring at room temperature for another 2 hours. The reaction mixture was quenched with water (10 ml), then placed in a separatory funnel using methylene chloride (200 ml) as a rinse. The organic layer of methylene chloride was washed with water (5×100 ml) and brine (100 ml), then dried. Solvent removal followed by column chromatographic purification afforded 3.6 gms of the titled compound.

Provenance & Evidence