Ethanol → Ethyl 6-chloro-5-methylpicolinate

Participants

Reaction Steps

4,6-Dichloro-1-methyl-2-oxa-5-azabicyclo[2.2.2]oct-5-en-3-one (26-3) (3.0 g, 14.4 mmol, 1 eq) was dissolved in chloroform (30 mL) and DBU (6.5 mL, 43 mmol, 3 eq) was added. After 5 minutes of stirring at ambient temperature, ethanol (0.84 mL, 16 mmol, 1.1 eq) was added and there was a slight exotherm. After 15 minutes of stirring at ambient temperature, the reaction mixture was concentrated and the crude residue was purified by flash chromatography (80 g SiO2, 0-100% EtOAc in hexanes) to afford ethyl 6-chloro-5-methylpyridine-2-carboxylate (26-4) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.97 (d, J=7.6 Hz, 1 H); 7.69 (d, J=7.6 Hz, 1 H); 4.47 (q, J=7.2 Hz, 2 H); 2.46 (s, 3 H); 1.43 (t, J=7.2 Hz, 3H). LRMS m/z (M+H) 200.0 found, 200.0 required.

Provenance & Evidence