Water → HCID 23078577, compound

Temperature

-78 °C

3-Bromo-4-methylpyridine (500 mg) was dissolved in tetrahydrofuran (15 ml) under an argon atmosphere to prepare a solution. A 1.6 M n-butyllithium/hexane solution (2 ml) was added dropwise to the solution at −78° C., and the mixture was then stirred at −78° C. for 30 min. A solution of 4,5-dimethylfurfural (350 mg) in tetrahydrofuran (2 ml) was added dropwise thereto, and the temperature of the reaction solution was raised to room temperature while stirring. Water was added to the reaction solution to stop the reaction, and the solvent was removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate 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)-(4-methylpyridin-3-yl)-methanol (174 mg, yield 28%).

1. customto prepare a solution
2. temperaturethe temperature of the reaction solution was raised to room temperature
3. stirringwhile stirring
4. customthe reaction
5. customthe solvent was removed by distillation under the reduced pressure
6. additionWater was added to the residue
7. extractionthe mixture was extracted with ethyl acetate
8. washThe ethyl acetate layer was then washed with water
9. dry with materialwas dried over anhydrous sodium sulfate
10. customThe solvent was removed by distillation under the reduced pressure
11. customthe residue was purified by column chromatography

ORD record

ord-9c4c4eecf25348b993af8f66a413681c

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560558B2