반응 #1069876

반응 방정식

4-(4-Pyridin-2-yl-but-3-ynyl)-benzonitrile

DMA

→

4-indolizin-3-ylmethyl-benzonitrile

수율 92.8%

용매

ethyl acetate

반응 조건

후처리

1. 1
   기타A dried 1 L of three-neck round-bottom flask was flushed with N2
2. 2
   기타connected to a N2 inlet
3. 3
   기타equipped with a thermometer and a magnetic stirrer
4. 4
   기타resulting in a light brown solution
5. 5
   workup.STIRRINGAfter stirring for 3 h at 130° C.
6. 6
   온도cooled to room temperature
7. 7
   기타The reaction was then quenched with water (300 mL), and ethyl acetate (400 mL)
8. 8
   workup.ADDITIONwas added
9. 9
   여과The resulting dark brown mixture was then filtered through a celite cake
10. 10
    기타to give a clear two-layer mixture
11. 11
    기타After separation
12. 12
    기타drying
13. 13
    농축concentration
14. 14
    기타a dark oil was obtained
15. 15
    workup.STIRRINGstirred for 20 minutes
16. 16
    여과After filtration through a celite cake
17. 17
    세척the filtrate was washed with water (100 mL) twice
18. 18
    건조dried over sodium sulfate
19. 19
    농축Concentration

실험 절차

A dried 1 L of three-neck round-bottom flask was flushed with N2, connected to a N2 inlet, equipped with a thermometer and a magnetic stirrer. 4-(4-Pyridin-2-yl-but-3-ynyl)-benzonitrile (58.73 g, 0.25 mol), DMA (490 mL) and TEA (70 mL) were successively added to the flask, resulting in a light brown solution. CuCl (25.05 g, 0.25 mol) was then added, after which the reaction turned dark brown. The reaction mixture was kept stirring at 130° C. After stirring for 3 h at 130° C., the reaction was complete, and cooled to room temperature. The reaction was then quenched with water (300 mL), and ethyl acetate (400 mL) was added. The resulting dark brown mixture was then filtered through a celite cake to give a clear two-layer mixture. After separation, drying, and concentration, a dark oil was obtained. The dark oil was dissolved in 250 mL of ethyl acetate, applied to 15 g of decoloring carbon, and stirred for 20 minutes. After filtration through a celite cake, the filtrate was washed with water (100 mL) twice, dried over sodium sulfate. Concentration gave 53.89 g (89%) of 4-indolizin-3-ylmethyl-benzonitrile. 1H NMR (CDCl3): δ (ppm) 7.55 (d, J=8.1 Hz, 2H); 7.50 (d, J=9.0 Hz, 1H); 7.39 (d, J=9.0 Hz, 1H); 7.23 (d, J=7.8 Hz, 2H); 6.64 (m, 2H), 6.44 (m, 2H); 4.27 (s, 2H). ESMS calcd. (C16H12N2): 232.1. found: 233.1 (M+H)+.

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