3-Cyanopyridine → HCID 69845219, compound

Participants

Reaction Steps

In an atmosphere of argon, activated zinc powder (4.88 g, 0.07 g atom) was suspended in anhydrous tetrahydrofuran (THF) (25.0 ml) to which was subsequently added dropwise several drops of ethyl bromoacetate while heating under reflux. When color of the reaction solution became green, 3-cyanopyridine (1.59 g, 15.0 mmol) was added to the solution, ethyl bromoacetate (6.0 ml, 51.4 mmol) was added dropwise thereto spending 50 minutes and then the mixture was heated under reflux for 15 minutes. After cooling, the reaction solution was diluted with THF, mixed with 50% potassium carbonate aqueous solution (15.0 ml) and then stirred for 30 minutes. After standing, the organic layer was collected and extracted three times with THF in the same manner and then the thus obtained organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=2:1-4:1) to obtain the title compound (2.26 g, 72.3%) as pale yellow oil.

Provenance & Evidence