Methyl iodide → 2-Ethyl-6-methylpyridine

Temperature

-40 °C

In a 250-ml 3-neck jacketed reactor flask, 4.3 g (40.2 mmol) of 2,6-dimethylpyridine and 4.06 g (40.2 mmol) of triethylamine were dissolved by addition of 50 ml of anhydrous tetrahydrofuran, and the solution was cooled to −40° C., after which 28.7 ml (46 mmol) of 1.6 M n-butyllithium in hexane was added dropwise thereto. At the same time, the solution changed to deep red. Next, the solution was stirred for 1 hour, and then warmed to 0° C., after which 5.7 g (40.2 mmol) of methyl iodide was added dropwise thereto, followed by stirring for 1 hour. Then, the reaction product was concentrated, and the concentrate was dissolved in ethyl acetate, washed with water and saline, dried with anhydrous magnesium sulfate, and then concentrated again, thereby obtaining crude 2-ethyl-6-methylpyridine.

1. temperaturewarmed to 0° C.
2. stirringby stirring for 1 hour
3. concentrationThen, the reaction product was concentrated
4. dissolutionthe concentrate was dissolved in ethyl acetate
5. washwashed with water and saline
6. dry with materialdried with anhydrous magnesium sulfate
7. concentrationconcentrated again

ORD record

ord-d60f24c15b334d498118458b9fa96ff7

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309371B2