2,4-Dimethylpyridine → Methyl (2-methylpyridin-4-yl)acetate

Temperature

0 °C

An LDA-THF solution (2.00 mol/L, 65.0 mL, 130 mmol) was cooled to −78° C., then a THF solution (50.0 mL) of 2,4-lutidine (10.7 g) was added thereto, followed by stirring for 2 hours. Then, the temperature was raised to 0° C., and a THF solution (50.0 mL) of dimethyl carbonate (11.7 g) was added dropwise to the mixture, followed by stirring for 30 minutes. Water was added to the reaction mixture, and the resulting mixture was concentrated under reduced pressure and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give methyl 2-methylpyridin-4-ylacetate (2.69 g, yield 16%).

1. stirringby stirring for 30 minutes
2. concentrationthe resulting mixture was concentrated under reduced pressure
3. extractionextracted with ethyl acetate
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

ORD record

ord-c22d69788dc145309b9d958b8a2a07ae

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07956060B2