Methanol → HCID 14837016, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride in an oil dispersion (8.0 g of 60 percent, 0.20 mol) was extracted with hexane to remove oil and suspended in 30 ml of tetrahydrofuran and to this 5.5 ml (0.14 mol) of anhydrous methanol was added dropwise with stirring. After about 10 min, 9.16 g (0.05 mol) of 2,3-difluoro-5-(trifluoromethyl)-pyridine was added. An exothermic reaction ensued which increased the temperature to about 60° C. The mixture was then heated at reflux for 6 hours and then a small amount of methanol was added. The mixture was allowed to cool and was thereafter poured onto ice. The resulting mixture was extracted several times with ether. The combined ether extracts were dried over sodium sulfate and concentrated by evaporation under reduced pressure to obtain 9.0 g (87 percent of theory) of the title compound as a white crystalline solid melting at 22°-23.5° C. The proton nmr spectrum was consistent with the assigned structure.

Provenance & Evidence