2-Methoxyethanol → 3-(2-Methoxyethoxy)pyridine-2-carboxylic acid

Participants

Reaction Steps

3-Fluoropyridine-2-carboxylic acid (150 mg, 1.06 mol), 2-methoxyethanol (1.5 mL) and potassium tert-butoxide (356 mg, 3.18 mmol) were charged to a sealed tube under nitrogen then stirred at 100 C for 18 h. The mixture was then diluted with water (3 mL), 1M HCl was added to bring the solution to pH 5 and the mixture was extracted with DCM (2×5 mL). 1M HCl was added to the aqueous layer to bring the solution to pH 3 and the mixture was extracted with DCM (2×5 mL). The combined organic extractions were dried over sodium sulfate and evaporated under vacuum to afford the title compound as a brown gum (54 mg, 26%). Method C HPLC-MS: MH+ requires m/z=198. Found: m/z=198, Rt=0.29 min.

Provenance & Evidence