Ethyl Acetate → 4-(Diethoxymethyl)pyridine

Participants

Reaction Steps

4-Pyridinecarboxaldehyde (3.00 mL, 31.4 mmol), ethyl orthoformate (15.7 mL, 94.2 mmol) and p-toluenesulfonic acid (229 mg, 1.57 mmol) were dissolved in ethanol (60.0 mL), and the mixture was heated to reflux under a nitrogen atmosphere for 10 hours. The reaction was stopped by addition of a saturated aqueous sodium bicarbonate solution 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 silica gel column chromatography (hexane/ethyl acetate=1/1) to give 4-(diethoxymethyl)pyridine (4.41 g, yield: 78%).

Provenance & Evidence