반응 #66149

반응 방정식

HCl

n-Butyl lithium

2-(4-bromo-phenyl)-1,1,1,3,3,3-hexamethyl-disilazane

4′,6′-dimethyl-2,3,5,6-tetrahydro-[1,2′]bipyridinyl-4-one

sodium hydroxide

→

4-(4-amino-phenyl)-4′,6′-dimethyl-3,4,5,6-tetrahydro-2H-[1,2′]-bipyridinyl-4-ol

수율 57.2%

용매

diethyl ether

tetrahydrofuran

반응 조건

후처리

1. 1
   온도then cooled in an ice bath
2. 2
   온도the resulting mixture heated at 50° C. for 2.5 h
3. 3
   기타was brought to room temperature
4. 4
   workup.STIRRINGstirred overnight
5. 5
   온도cooled to 0° C.
6. 6
   기타quenched into ammonium chloride solution
7. 7
   추출The mixture was extracted with ethyl acetate
8. 8
   세척the organic phase was washed with water, brine
9. 9
   건조dried over anhydrous sodium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated in vacuo
12. 12
    기타to yield the crude compound
13. 13
    workup.STIRRINGthe resulting mixture was stirred overnight at room temperature
14. 14
    추출the mixture was extracted with chloroform
15. 15
    건조The organic phase was dried over anhydrous sodium sulfate
16. 16
    여과filtered
17. 17
    농축concentrated to dryness
18. 18
    기타to give a viscous red oil which
19. 19
    기타was purified
20. 20
    세척by washing with pentane (5×10 mL)

실험 절차

n-Butyl lithium (1 mL, 1.6 M in hexane, 1.6 mmol) was added dropwise to a solution of 2-(4-bromo-phenyl)-1,1,1,3,3,3-hexamethyl-disilazane (0.7 g, 2.20 mmol) in dry diethyl ether (10 mL) and stirred at room temperature for 15 min then cooled in an ice bath. A solution of 4′,6′-dimethyl-2,3,5,6-tetrahydro-[1,2′]bipyridinyl-4-one (0.3 g, 1.47 mmol) in dry tetrahydrofuran (15 mL) was added and the resulting mixture heated at 50° C. for 2.5 h. The reaction mixture was brought to room temperature and stirred overnight, then cooled to 0° C. and quenched into ammonium chloride solution. The mixture was extracted with ethyl acetate and the organic phase was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield the crude compound, to which was added 2N HCl and the resulting mixture was stirred overnight at room temperature. The pH of the solution was adjusted to pH 10 with dilute sodium hydroxide then the mixture was extracted with chloroform. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give a viscous red oil which was purified by washing with pentane (5×10 mL) to afford 4-(4-amino-phenyl)-4′,6′-dimethyl-3,4,5,6-tetrahydro-2H-[1,2′]-bipyridinyl-4-ol (0.25 g, 57%).

출처