반응 #1447097

반응 방정식

Sodium borohydride

N-[4-bromo-2-(4-ethyl-benzoyl)-5-methoxy-phenyl]-acetamide

→

desired product

N-[4-Bromo-2-(4-ethyl-benzyl)-5-methoxy-phenyl]-acetamide

용매

ethanol

반응 조건

후처리

1. 1
   기타The cooling bath is removed
2. 2
   workup.ADDITIONThen, 1 M aqueous NaOH solution (8.5 mL) is added
3. 3
   농축the resulting solution is concentrated under reduced pressure
4. 4
   workup.ADDITIONWater is added to the residue
5. 5
   추출the resulting mixture is extracted with ethyl acetate
6. 6
   세척The combined organic extracts are washed with brine
7. 7
   건조dried (Na2SO4)
8. 8
   농축concentrated
9. 9
   workup.ADDITIONtriethylsilane (4.3 mL) is added
10. 10
    workup.STIRRINGThe solution is stirred at ambient temperature overnight
11. 11
    workup.ADDITIONpoured
12. 12
    기타on crushed ice
13. 13
    추출The resultant mixture is extracted twice with ethyl acetate
14. 14
    세척The combined extracts are washed with brine
15. 15
    건조dried (sodium sulphate)
16. 16
    농축concentrated under reduced pressure
17. 17
    workup.ADDITIONThe residue is treated with methanol
18. 18
    기타the precipitate formed
19. 19
    기타is separated
20. 20
    세척The precipitate is then washed with diisopropylether
21. 21
    기타dried

실험 절차

Sodium borohydride (0.17 g) is added portionwise to an ice-cold suspension of N-[4-bromo-2-(4-ethyl-benzoyl)-5-methoxy-phenyl]-acetamide (3.25 g) in ethanol (50 mL). The cooling bath is removed and the solution is stirred at ambient temperature for 2 h. Then, 1 M aqueous NaOH solution (8.5 mL) is added and the resulting solution is concentrated under reduced pressure. Water is added to the residue and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are washed with brine, dried (Na2SO4) and concentrated. The residue is taken up in trifluoroacetic acid (20 mL) and triethylsilane (4.3 mL) is added. The solution is stirred at ambient temperature overnight and then poured on crushed ice. The resultant mixture is extracted twice with ethyl acetate. The combined extracts are washed with brine, dried (sodium sulphate) and concentrated under reduced pressure. The residue is treated with methanol and the precipitate formed is separated. The precipitate is then washed with diisopropylether and dried to give the desired product.

출처