4-Nitrobenzaldehyde → 4-Nitrobenzyl alcohol

Temperature

-78 °C

To a solution of 2-bromo-3-methoxypyridine (1.00 g) in diethylether (20 ml) was added a solution of n-butyllithium in hexane (1.6M, 3.7 ml) at −78° C., and the mixture was stirred for 1 hour to prepare the lithium salt, which was dropwise added to a solution of 4-nitrobenzaldehyde (0.81 g) in tetrahydrofuran (10 ml) cooled at −78° C. The mixture was stirred at −78° C. To the reaction mixture was added water to stop the reaction, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated. Under reduced pressure, the residue was separated and purified with column chromatography (ethyl acetate/hexane=1:3→1:1) to give 3-methoxypyridin-2-yl)-(4-nitrophenyl)methanol (742 mg) as pale yellow crystals.

1. stirringThe mixture was stirred at −78° C
2. customthe reaction
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with saturated sodium chloride solution
5. dry with materialdried with magnesium sulfate
6. concentrationconcentrated
7. customUnder reduced pressure, the residue was separated
8. custompurified with column chromatography (ethyl acetate/hexane=1:3→1:1)

ORD record

ord-801904651da1432eb9aab88b607bee4d

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06268354B1