Ethyl Acetate → alpha-(1,1-Dimethylethyl)-3-pyridinemethanol

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Reaction Steps

3-Pyridinecarboxaldehyde (200 μL, 2.12 mmol) was dissolved in tetrahydrofuran (5.0 mL). To this, tert-butyllithium (a 1.46 mol/L solution in pentane, 4.37 mL, 6.36 mmol) was added dropwise 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, hexane/ethyl acetate=1/1) to give 3-(2,2-dimethyl-1-hydroxypropyl)pyridine (Compound CG) (64.0 mg, yield: 18%).

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