3-Cyanopyridine → (4,5-Dimethylfuran-2-yl)-(3-pyridyl)-methanone

Temperature

0 °C

2,3-Dimethylfuran (5 g) was dissolved in diethyl ether (75 ml) under an argon atmosphere, a 1.6 M hexane solution (35.7 ml) of n-butyllithium was added dropwise thereto at 0° C., and the mixture was stirred under reflux for 2.5 hr. Thereafter, the reaction solution was cooled to −78° C., a solution of 3-cyanopyridine (6.0 g) in diethyl ether (20 ml) was added dropwise thereto, and the mixture was stirred at room temperature for 3 hr. The reaction solution was poured into ice to stop the reaction solution. The reaction solution was adjusted to pH 5 by the addition of 2 M hydrochloric acid and was extracted with chloroform. The chloroform layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using hexane-ethyl acetate to give (4,5-dimethylfuran-2-yl)-(3-pyridyl)-methanone (1.9 g, yield 18%).

1. temperatureunder reflux for 2.5 hr
2. temperatureThereafter, the reaction solution was cooled to −78° C.
3. stirringthe mixture was stirred at room temperature for 3 hr
4. additionThe reaction solution was poured into ice
5. extractionwas extracted with chloroform
6. washThe chloroform layer was then washed with water
7. dry with materialwas dried over anhydrous sodium sulfate
8. customThe solvent was removed by distillation under the reduced pressure
9. customthe residue was purified by column chromatography

ORD record

ord-00de61681a0b4b3ea3b18142c91a55d7

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560558B2