Water → (2-Methoxy-4-nitrophenyl)(pyridin-2-yl)methanol

2-bromopyridine (1.4 ml) was dissolved in diethylether (40 ml), and the mixture was cooled to −78° C. under argon atmosphere 1.6M n-butyllithium hexane solution (9.1 ml) was added dropwise to the solution, and the mixture was stirred for 30 minutes. The reaction solution was added dropwise to a solution of 2-methoxy-4-nitrobenzaldehyde (2.4 g) in tetrahydrofuran (600 ml) under argon atmosphere at −78° C. The mixture was allowed to be at room temperature and stirred overnight, water was added to the mixture, and the mixture was concentrated. The mixture was extracted with ethyl acetate, organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane), to give (2-methoxy-4-nitrophenyl)(pyridin-2-yl)methanol (1.9 g) as pale yellow crystals.

1. additionwas added dropwise to the solution
2. customto be at room temperature
3. stirringstirred overnight
4. concentrationthe mixture was concentrated
5. extractionThe mixture was extracted with ethyl acetate, organic layer
6. washwas washed with water and saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. distillationthe solvent was distilled off
9. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane)

ORD record

ord-798cc7ba8e8441cfad05b3fa46deb56a

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262185B2