Acetophenone → 1-phenyl-3-(pyridin-2-yl)propane-1,3-dione

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Reaction Steps

Acetophenone (11.6 mL, 99 mmol), was added to a suspension of potassium tert-butoxide (12.34 g 110 mmol) in toluene (150 mL) and stirred under argon. The flask was then charged with ethyl picolinate (13.4 mL, 99 mmol) and the mixture stirred overnight. The toluene was removed by rotary evaporation and 200 mL of both diethylether and deionised water added. With stirring the mixture was acidified with dilute HCl until the ether layer was dark orange˜pH 7). The ether layer was separated, washed with deionised water (3×100 mL), dried over magnesium sulfate and filtered. The solvent was removed and the solid recrystallised from hot ethanol to yield 1-phenyl-3-pyridin-2-ylpropane-1,3-dione (1) as a pale yellow crystalline solid (15.3 g, 69%).

Provenance & Evidence