2-Pyridinecarboxaldehyde → HCID 86744857, compound

Participants

Reaction Steps

To a solution of ethyl isobutyrylacetate (15.78 g, 99.7 mmol) and pyridine-2-carboxaldehyde (10.7 g, 99.9 mmol) in dry benzene (100 mL) at room temperature under argon was added acetic acid (0.30 mL, 5.2 mmol) and piperidine (0.80 mL, 8.1 mmol). After stirring at room temperature for 1 hour and at reflux for 3 hours, the cooled mixture was washed with water, saturated NaHCO3 and saturated NaCl solutions, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with ethyl acetate (EtOAc)-hexane (1:9) to give title compound (20.61 g, 83%) as an orange, viscous oil which crystallized on standing to a semi-solid mass, mp 53°-55° C.

Provenance & Evidence