4-Nitrobenzaldehyde → 2-Pyridinemethanol,a-(4-nitrophenyl)-

Temperature

-78 °C

To a solution cooled at −78° C. of 2-bromopyridine (10.0 g) in diethylether (200 ml) was dropwise added 1.6M butyllithium hexane solution (39.6 ml) for 10 minutes. The mixture was stirred at −78° C. for 1 hour, and to the mixture was dropwise added a solution of 4-nitrobenzaldehyde in THF (50 ml). The reaction mixture was stirred at −78° C. for 3 hours, and to the mixture was added water (100 ml). The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/toluene=1/2) and re-crystallized from diisopropylether to give (4-nitro-phenyl)-(2-pyridyl)methanol (4.50 g) as orange crystals.

1. customfor 10 minutes
2. stirringThe reaction mixture was stirred at −78° C. for 3 hours
3. extractionThe mixture was extracted with ethyl acetate
4. washthe organic layer was washed with saturated sodium chloride solution
5. dry with materialdried with anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was separated
8. custompurified with column chromatography (ethyl acetate/toluene=1/2)
9. customre-crystallized from diisopropylether

ORD record

ord-6c36dc1aefa44b9491c36f1300022355

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06268354B1