Boron trifluoride etherate → (2-Chloropyridin-4-yl)methanol

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Reaction Steps

Boron trifluoride diethyl etherate (71 g, 0.5 mol) was added dropwise to a suspension of 2-chloroisonicotinic acid (20 g, 0.125 mol) and sodium borohydride (14.3 g, 0.376 mol) in THF (200 mL) with stirring at −10˜−5° C., then the mixture was stirred at room temperature overnight. The reaction mixture was quenched with water (100 mL), and extracted with ethyl acetate (3×200 mL). The organic layers were combined, washed with brine (200 mL), dried over anhydrous Na2SO4, filtered and concentrated to dryness. The crude material was further purified by silica gel chromatography (EtOAc/Hexane=1/4) and afforded 2-chloro-4-(hydroxymethyl)pyridine (15.4 g, 85.8% yield) as an oil.

Provenance & Evidence