Hydrochloric Acid → (4,5-Dimethylfuran-2-yl)-(2-pyridyl)-methanone

Temperatur

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 2-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. The reaction solution was adjusted to pH 5 by the addition of 2 M hydrochloric acid and was then 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)-(2-pyridyl)-methanone (1.8 g, yield 17%).

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. customthe reaction
6. extractionwas then extracted with chloroform
7. washThe chloroform layer was then washed with water
8. dry with materialwas dried over anhydrous sodium sulfate
9. customThe solvent was removed by distillation under the reduced pressure
10. customthe residue was purified by column chromatography

ORD-Eintrag

ord-4709ba83186d4c28af7547d3e5d405a5

Quelldatensatz

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07560558B2