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

温度

-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-nitrophenyl)-(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レコード

ord-cdb1b633e1a44edaaaf5441e2ff19b06

出典データセット

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06172061B2