반응 #929214

반응 방정식

methyl 2-chloronicotinate

phenyltributyltin

lithium chloride

→

Methyl 2-phenylnicotinate

용매

toluene

반응 조건

후처리

1. 1
   기타was degassed
2. 2
   온도at reflux for 5 hours
3. 3
   기타The cooled reaction mixture
4. 4
   여과was filtered
5. 5
   기타the filtrate evaporated
6. 6
   기타the residue partitioned between acetonitrile (50 ml) and hexane (5×20 ml)
7. 7
   추출The combined hexane layers were extracted with hydrochloric acid (lM, 4×10 ml)
8. 8
   세척the extracts washed with ethyl acetate (15 ml), and basified (4M NaOH)
9. 9
   추출The resulting suspension was extracted with dichloromethane (4×10 ml)
10. 10
    건조the combined extracts dried over MgSO4
11. 11
    기타evaporated
12. 12
    기타to leave a colourless oil
13. 13
    기타Meanwhile, the acetonitrile layer from above was evaporated
14. 14
    workup.DISSOLUTIONthe residual oil dissolved in diethyl ether (50 ml)
15. 15
    추출ethyl acetate (25 ml) and the solution extracted with hydrochloric acid (1M, 4×10 ml)
16. 16
    추출Basification of the acid extracts (4M NaOH) and extraction of the resulting suspension with dichloromethane (4×10 ml)
17. 17
    건조by drying of the combined extracts with MgSO4 and evaporation
18. 18
    기타gave an oil which
19. 19
    기타that obtained

실험 절차

A mixture of methyl 2-chloronicotinate (3.10 g, 18.1 mmol), phenyltributyltin (6.30 g, 17 mmol), lithium chloride (5.04 g, 120 mmol), and tetrakis(triphenylphosphine)palladium (1.12 g, 1 mmol) in toluene (65 ml) was degassed and then stirred under a nitrogen atmosphere overnight at 90° C. and at reflux for 5 hours. The cooled reaction mixture was filtered, the filtrate evaporated, and the residue partitioned between acetonitrile (50 ml) and hexane (5×20 ml). The combined hexane layers were extracted with hydrochloric acid (lM, 4×10 ml), the extracts washed with ethyl acetate (15 ml), and basified (4M NaOH). The resulting suspension was extracted with dichloromethane (4×10 ml), the combined extracts dried over MgSO4 and evaporated to leave a colourless oil. Meanwhile, the acetonitrile layer from above was evaporated and the residual oil dissolved in diethyl ether (50 ml) and ethyl acetate (25 ml) and the solution extracted with hydrochloric acid (1M, 4×10 ml). Basification of the acid extracts (4M NaOH) and extraction of the resulting suspension with dichloromethane (4×10 ml) followed by drying of the combined extracts with MgSO4 and evaporation gave an oil which was combined with that obtained as described above (2.62 g).

출처