Water → HCID 22938783, compound

Temperature

-78 °C

2-bromo-4-methylpyridine (1.5 ml) was dissolved in diethylether (50 ml), and the mixture was cooled to −78° C. under argon atmosphere. 1.6M n-butyllithium hexane solution (8.3 ml) was added dropwise to the solution, and the mixture was stirred for 40 minutes. The reaction solution was added dropwise to a solution of 2-ethoxy-4-nitrobenzaldehyde (2.2 g) in tetrahydrofuran (200 ml) under argon atmosphere at −78° C. The mixture was allowed to be at room temperature and stirred overnight, and water was added to the mixture. The mixture was concentrated and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and then, the solvent was evaporated. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane), to give (2-ethoxy-4-nitrophenyl)(4-methylpyridin-2-yl)methanol (1.9 g) as brown crystals.

1. customto be at room temperature
2. stirringstirred overnight
3. concentrationThe mixture was concentrated
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with water and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customthe solvent was evaporated
8. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane)

ORD record

ord-f25203d8092747488427ed98906519ed

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262185B2