4-Nitrobenzaldehyde → (3-Methoxymethoxypyridin-2-yl)-(4-nitrophenyl)methanol

Temperature

-78 °C

Under nitrogen atmosphere, to a solution of 2-bromo-3-methoxymethoxypyridine (10.00 g) in diethylether (150 ml) was added a solution of n-butyllithium in hexane (1.6M, 31.5 ml) at −78° C., and the mixture was stirred for 1 hour to prepare the lithium salt. The resulting lithium salt was dropwise added to a solution of 4-nitrobenzaldehyde (6.93 g) in tetrahydrofuran (100 ml) cooled at −78° C., and the mixture was stirred at the same temperature for 3 hours. 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→1:2) to give (3-methoxymethoxypyridin-2-yl)—(4-nitrophenyl)-methanol (11.78 g) as yellow oil.

1. stirringthe mixture was stirred at the same temperature for 3 hours
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 under reduced pressure
7. customThe residue was separated
8. custompurified with column chromatography (ethyl acetate/hexane=1:3→1:2)

ORD record

ord-7db39247387746ba8d1be423be2905e2

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06413947B1