Methanol → HCID 14837016, compound

Temperature

60 °C

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.

1. extractionSodium hydride in an oil dispersion (8.0 g of 60 percent, 0.20 mol) was extracted with hexane
2. customto remove oil
3. additionwas added dropwise
4. customAn exothermic reaction
5. temperatureThe mixture was then heated
6. temperatureat reflux for 6 hours
7. temperatureto cool
8. additionwas thereafter poured onto ice
9. extractionThe resulting mixture was extracted several times with ether
10. dry with materialThe combined ether extracts were dried over sodium sulfate
11. concentrationconcentrated by evaporation under reduced pressure

ORD record

ord-bf39896f640a491a8156732747f8977f

Source dataset

uspto-grants-1990_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04931452