2,5-Dimethylpyridine → 1-(5-Methylpyridin-2-yl)propan-2-one

Temperature

0 °C

To a stirred solution of 2,5-lutidine (2.68 g) in tetrahydrofuran (16 ml) was added a solution of n-butyllithium in n-hexane (1.66M, 16.6 ml) dropwise at −50° C. under a nitrogen atmosphere, and the mixture was warmed to 0° C. The mixture was cooled to −50° C., and N,N-dimethylacetamide (2.56 ml) was added dropwise. Then the mixture was warmed to room temperature, poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate (100 ml×3). The combined organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 100 g, n-hexane:ethyl acetate=1:2) to give 1-(5-methylpyridin-2-yl)propan-2-one (2.60 g).

1. temperatureThe mixture was cooled to −50° C.
2. temperatureThen the mixture was warmed to room temperature
3. extractionextracted with ethyl acetate (100 ml×3)
4. washThe combined organic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. customevaporated under reduced pressure
7. customThe residue was purified by column chromatography (silica gel 100 g, n-hexane:ethyl acetate=1:2)

ORD record

ord-a52571cb6a074d5f8151bbb83cb4ee6a

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06521643B1