General procedure for the synthesis of (5-fluoropyridin-2-yl)methanol from ethyl 5-fluoropyridine-2-carboxylate: to a solution of ethyl 5-fluoropyridine-2-carboxylate (377 mg, 2.23 mmol) in tetrahydrofuran (6 mL) was slowly added lithium aluminum hydride (LiAlH4, 73 mg, 3.34 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, it was quenched with ice water and the organic layer was subsequently extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with ethyl acetate/hexane (20:80 to 60:40) as eluent to give (5-fluoropyridin-2-yl)methanol (309 mg, 54% yield, colorless oil).
