반응 #653172

반응 방정식

2-bromo-3-methoxypyridine

n-butyllithium

4-nitrobenzaldehyde

lithium

→

(4-nitrophenyl)methanol

수율 90.4%

용매

diethylether

hexane

water

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at −78° C
2. 2
   기타the reaction
3. 3
   추출the mixture was extracted with ethyl acetate
4. 4
   세척The organic layer was washed with saturated sodium chloride solution
5. 5
   건조dried with magnesium sulfate
6. 6
   농축concentrated
7. 7
   기타Under reduced pressure, the residue was separated
8. 8
   기타purified with column chromatography (ethyl acetate/hexane=1:3→1:1)

실험 절차

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.

출처