Acetic Acid → HCID 68227064, compound

Participants

Reaction Steps

To a solution of ethyl 5-chloro-3-(2-ethoxy-2-oxoethoxy)picolinate (385 mg, 1.34 mmol) in toluene (10 ml) at 23° C. was added sodium ethoxide (200 mg, 2.94 mmol) and the reaction mixture was stirred at reflux overnight. To the yellow suspension was added some ice, ethyl acetate and set to pH=4 with acetic acid. The organic layer was separated and washed with sat NaHCO3 solution. The aqueous layers were reextracted with ethyl acetate, then dried over Na2SO4, filtered and evaporated to give the crude ethyl 6-chloro-3-hydroxyfuro[3,2-b]pyridine-2-carboxylate (154 mg, 637 μmol, 47.6% yield) as a light brown solid. MS (ISN): m/z=240.1 [(M−H)−] and 242.3 [(M+2−H)−].

Provenance & Evidence