Thionyl Chloride → 3-Methoxy-4-ethyl-6-(1-chloroethyl)-pyridine

Participants

Reaction Steps

A solution of 3-methoxy-4-ethyl-6-(1-hydroxyethyl)-pyridine (236 mg, 1.3 mmol) in 5 mL of methylene chloride at 0° C. is treated with thionyl chloride (0.141 mL, 1.95 mmol) and stirred at room temperature for 1 h. The reaction is quenched with 12 mL of saturated sodium bicarbonate. The aqueous layer is extracted with 3×10 mL of methylene chloride. The combined organics are dried over potassium carbonate and concentrated in vacuo to provide 249 mg (96%) of 3-methoxy-4-ethyl-6-(1-chloroethyl)-pyridine.

Provenance & Evidence