반응 #1605780

반응 방정식

2-bromo-5-methylpyridine

acetonitrile

n-butyl lithium

→

2-(5-methylpyridin-2-yl) acetonitrile

수율 80.7%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.WAITThe reaction mixture was kept at minus 78° C. for 1 hour
2. 2
   온도warmed up slowly to room temperature
3. 3
   workup.STIRRINGstirred for another hour
4. 4
   기타the layer was separated
5. 5
   세척The organic layer was washed with water and brine
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   기타evaporated
9. 9
   기타to give 18 g of crude product
10. 10
    기타The crude product was purified by silica-gel column chromatography (eluent, PE/EtOAc=15:1)

실험 절차

To a solution of anhydrous acetonitrile (10.1 mL, 191.83 mmol, 3.3 equiv.) in dry THF (500 mL) was added dropwise n-butyl lithium (2.5 M in hexane, 69.8 mL, 174.39 mmol, 3 equiv.) at minus 78° C. under nitrogen atmosphere. The resulting white suspension was stirred at minus 78° C. for 1 hour, and then a solution of 2-bromo-5-methylpyridine (10.0 g, 58.13 mmol, 1 equiv.) in dry THF (30 mL) was added. The reaction mixture was kept at minus 78° C. for 1 hour and then warmed up slowly to room temperature and stirred for another hour. Ice water was added and the layer was separated. The organic layer was washed with water and brine, dried over MgSO4, filtered, and evaporated to give 18 g of crude product. The crude product was purified by silica-gel column chromatography (eluent, PE/EtOAc=15:1) to give 2-(5-methylpyridin-2-yl) acetonitrile (6.2 g, yield 80%). 1H NMR (300 MHz, CDCl3): δ 8.40 (d, J=3.0 Hz, 1H), 7.54 (dd, J1=3.0 Hz, J2=6.0 Hz, 1 H), 7.32 (d, J=6.0 Hz, 1 H), 3.90 (s, 2H), 2.40 (s, 3H).

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