반응 #1687620

반응 방정식

2

3-Cyano-1-methylpyridinium Iodide

sodium borohydride

→

3Cyano-1-methyl-1,2,5,6-tetrahydropyridine

용매

methanol

water

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition the mixture
2. 2
   workup.DISTILLATIONMost of the methanol was distilled off
3. 3
   workup.ADDITIONTo the residue was added saturated ammonium chloride solution (200 ml)
4. 4
   추출the mixture was extracted three times with ether (300 ml)
5. 5
   세척The combined organ phases wee washed once with water
6. 6
   추출were then extracted three times with 4M hydrochloric
7. 7
   workup.WAITThe colored aqueous phases were kept for 1 hour at room temperature
8. 8
   추출The mixture was extracted three times with ether (250 ml)
9. 9
   기타the combined organic phases were separated from the solid byproducts
10. 10
    세척The organic phase was washed with 4 portions of saturated sodium chloride solution (200 ml)
11. 11
    건조dried over magnesium sulphate
12. 12
    기타evaporated

실험 절차

To a solution of 2 (133 g, 0.54 mol) in methanol (1000 ml) and water (200 ml) was added sodium borohydride (41 g, 1.08 mol) in portions at temperatures below 28° C. After the addition the mixture was stirred for 1 hour at room temperature. Most of the methanol was distilled off. To the residue was added saturated ammonium chloride solution (200 ml), and the mixture was extracted three times with ether (300 ml). The combined organ phases wee washed once with water and were then extracted three times with 4M hydrochloric and (300 ml). The colored aqueous phases were kept for 1 hour at room temperature, and pH was then adjusted to 14. The mixture was extracted three times with ether (250 ml), and the combined organic phases were separated from the solid byproducts. The organic phase was washed with 4 portions of saturated sodium chloride solution (200 ml), dried over magnesium sulphate and evaporated. This yielded 17.4 g (0.143 mol, 26%) of crude oily title compound, which was sufficiently pure according to the 1H NMR spectrum.

출처