Ethyl Acetate → alpha-Methyl-3-pyridinemethanol

Participants

Reaction Steps

To methylmagnesium bromide (a 0.96 mol/L solution in tetrahydrofuran, 16.6 mL, 15.9 mmol), a solution of 3-pyridinecarboxaldehyde (500 μL, 5.30 mmol) in tetrahydrofuran (5.0 mL) was slowly added under a nitrogen atmosphere at 0° C., and the mixture was stirred at the same temperature for 1. Then, a saturated aqueous ammonium chloride 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 silica gel column chromatography (chloroform/methanol 9/1) to give 3-(1-hydroxyethyl)pyridine (Compound CA) (498 mg, yield: 76%).

Provenance & Evidence