Reaktion #1447097

Reaktionsgleichung

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

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe cooling bath is removed
2. 2
   workup.ADDITIONThen, 1 M aqueous NaOH solution (8.5 mL) is added
3. 3
   Einengenthe resulting solution is concentrated under reduced pressure
4. 4
   workup.ADDITIONWater is added to the residue
5. 5
   Extraktionthe resulting mixture is extracted with ethyl acetate
6. 6
   WaschenThe combined organic extracts are washed with brine
7. 7
   Trocknendried (Na2SO4)
8. 8
   Einengenconcentrated
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
    Sonstigeon crushed ice
13. 13
    ExtraktionThe resultant mixture is extracted twice with ethyl acetate
14. 14
    WaschenThe combined extracts are washed with brine
15. 15
    Trocknendried (sodium sulphate)
16. 16
    Einengenconcentrated under reduced pressure
17. 17
    workup.ADDITIONThe residue is treated with methanol
18. 18
    Sonstigethe precipitate formed
19. 19
    Sonstigeis separated
20. 20
    WaschenThe precipitate is then washed with diisopropylether
21. 21
    Sonstigedried

Vorschrift

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.

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