2,2,2-Trifluoroethanol → 5-Methyl-6-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-5-methyl-pyridine-2-carboxylic acid (CAN 1166828-13-2, 200 mg, 1.17 mmol), 2,2,2-trifluoroethanol (466 mg, 336 μl, 4.66 mmol) and 1,8-diazabicyclo(5.4.0)undec-7-ene (CAN 83329-50-4, 887 mg, 870 μl, 5.83 mmol) was shaken in a sealed tube for 2 days at 140° C. and subsequently for additional 5 days at 150° C. The brown solution was poured into 25 mL ice/0.1 N HCl and extracted with i-PrOAc (2×25 mL). The organic layers were washed with ice/brine (2×25 mL). The organic layers were dried over sodium sulfate and concentrated in vacuo to give the title compound (198 mg, 58%) as off-white solid containing traces of starting material, MS (EI): m/e=233.9 [M−H]−.

Provenance & Evidence