5-Chloro-2-pyridone → HCID 20326567, compound

Participants

Reaction Conditions

Reaction Steps

5-Chloro-2-pyridone (2.58 g.), silver carbonate (3.44 g.) and dry toluene (14 ml.) were stirred together under argon and heated to 65° C. for 20 minutes. A solution of 1-chloro-3-iodopropan-2-one (4 g.) in dry toluene (10 ml.) was added, and the mixture was stirred at 60°-65° C. for 3 hours, cooled, and filtered through "Hyflo" (trade mark) kieselguhr, washing the filter cake with toluene (15 ml.). The filtrate was evaporated to dryness, and the residue was purified by column chromatography on silica gel (100 g.), eluting with 10% v/v ethyl acetate in toluene. The first 130 ml. of eluate was discarded, and the next 60 ml. was collected, and evaporated to dryness to give 1-chloro-3-(5-chloropyrid-2-yloxy)propan-2-one, RF = 0.80 (50% v/v toluene in ethyl acetate).

Provenance & Evidence