反应 #742318

反应方程式

HCl

3-ethoxy-2-cyclopentenone

2-Bromopyridine

n-BuLi

→

3-(2-pyridyl)-2-cyclopenten-1-one

收率 62.0%

溶剂

THF

THF

反应条件

后处理

1. 1
   workup.STIRRINGstirred at 0° C. for 2 h
2. 2
   洗涤was washed with EtOAc
3. 3
   萃取extracted with CH2Cl2
4. 4
   洗涤The organic layer was washed with brine
5. 5
   干燥dried over anhyd Na2SO4
6. 6
   其他followed by the removal of solvent
7. 7
   其他The crude product was purified by column chromatography (Hexane/EtOAc=1/3)

实验过程

To a solution of 2-Bromopyridine (5.00 g, 31.6 mmol) in THF (30 ml) was added dropwise n-BuLi (2.55 M in Hexane, 12.5 mL. 31.9 mmol) at −78° C., and stirred for 10 min. To a reaction mixture was added dropwise 3-ethoxy-2-cyclopentenone (2.00 g, 15.9 mmol) in THF (10 mL) at −78° C., and stirred at 0° C. for 2 h. The reaction mixture was acidified with 2M HCl (10 mL), and aqueous layer was washed with EtOAc. The aqueous layer was basified with 1M NaOH aq., and then extracted with CH2Cl2. The organic layer was washed with brine, and dried over anhyd Na2SO4 followed by the removal of solvent. The crude product was purified by column chromatography (Hexane/EtOAc=1/3) to yield 3-(2-pyridyl)-2-cyclopenten-1-one (1.57 g, 58%) as brown solid.

来源