General procedure for the synthesis of 2-(chloromethyl)oxazole from 2-hydroxymethyl oxazole: Thionyl chloride (SOCl2, 3.25 mL, 45 mmol) was added slowly and dropwise to a solution of 2-hydroxymethyl oxazole (450 mg, 4.5 mmol) in dichloromethane (DCM, 25 mL) at 0 °C. The reaction mixture was stirred at 0 °C for 1 hour. Subsequently, water (50 mL) and ethyl acetate (EtOAc, 60 mL) were added to the reaction system for extraction. The organic and aqueous phases were separated, and the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 2-(chloromethyl)oxazole as a white solid (200 mg, 1.7 mmol, 37% yield).
