Ethylene Glycol → 3-(1,3-Dioxolan-2-yl)pyridine

Participants

Reaction Steps

3-Pyridinecarboxaldehyde (3.00 mL, 31.8 mmol), ethylene glycol (2.66 mL, 47.7 mmol) and p-toluenesulfonic acid (302 mg, 1.59 mmol) were suspended in toluene (100 mL). The mixture was heated to reflux under a nitrogen atmosphere for 2 hours, during which produced water was removed by use of a Dean-Stark trap. Then, a saturated aqueous potassium carbonate solution was added to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by column chromatography (hexane/ethyl acetate=1/1) to give 3-(1,3-dioxolan-2-yl)pyridine (4.27 g, yield: 89%).

Provenance & Evidence