Triethylamine → HCID 68227270, compound

Participants

Reaction Steps

Ethyl 2-(5-chloro-2-iodopyridin-3-yloxy)acetate (16.5 g, 48.3 mmol) was carbonylated with 20 bar carbon monoxide in the presence of bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane adduct (1.66 g, 2.03 mmol) in a mixture of ethanol, ethyl acetate and triethylamine at 70° C. for 20 h. The crude reaction mixture was extracted with ethyl acetate and water, the organic layer was dried over sodium sulfate. Removal of the solvent in vacuum left a dark brown oil, which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the ethyl 5-chloro-3-(2-ethoxy-2-oxoethoxy)picolinate (12.5 g, 43.4 mmol, 89.9% yield) as a light red solid. MS (ISP): m/z=287.9 [(M+H)+] and 290.1 [(M+2+H)+].

Provenance & Evidence