Sodium Methoxide → HCID 67209425, compound

Participants

Reaction Steps

3-(2-Methoxycarbonyl-ethyl)-5-methyl-pyridine-2-carboxylic acid methyl ester (2.33 g, 9.82 mmol) was dissolved in THF (70 ml). NaOMe (0.796 g, 14.7 mmol) was added and the reaction was heated at reflux temperature for 2 h. The solvents were evaporated under reduced pressure. The residue was taken into 4.5 N aqueous hydrochloric acid (24 ml) and the mixture was heated at reflux temperature for 2 h. After cooling to it solid potassium carbonate was added carefully in portions until pH >8. The mixture was extracted with DCM, the combined organic layers were washed with aq Na2CO3 and aq ammonium chloride solution, dried over sodium sulfate, and the solvent was evaporated at reduced pressure. The residue was purified by chromatography on silica (Flashmaster, hes/EtOAc 1/1 to EtOAc over 15 min, EtOAc to EtOAc/MeOH 9/1 over 10 min) to obtain the product as off-white solid (1.7 g, 81%). [1H-NMR (DMSO-d6, 600 MHz) δ 8.57 (s, 1H), 7.87 (s, 1H), 3.06 (t, 2H), 2.65 (t, 2H), 2.42 (s, 3H); LCMS RtI=2.460 min; [M+H]+=148.0]

Provenance & Evidence