Reacción #1447097

Ecuación de reacción

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

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe cooling bath is removed
2. 2
   workup.ADDITIONThen, 1 M aqueous NaOH solution (8.5 mL) is added
3. 3
   Concentraciónthe resulting solution is concentrated under reduced pressure
4. 4
   workup.ADDITIONWater is added to the residue
5. 5
   Extracciónthe resulting mixture is extracted with ethyl acetate
6. 6
   LavadoThe combined organic extracts are washed with brine
7. 7
   Secadodried (Na2SO4)
8. 8
   Concentraciónconcentrated
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
    Otroon crushed ice
13. 13
    ExtracciónThe resultant mixture is extracted twice with ethyl acetate
14. 14
    LavadoThe combined extracts are washed with brine
15. 15
    Secadodried (sodium sulphate)
16. 16
    Concentraciónconcentrated under reduced pressure
17. 17
    workup.ADDITIONThe residue is treated with methanol
18. 18
    Otrothe precipitate formed
19. 19
    Otrois separated
20. 20
    LavadoThe precipitate is then washed with diisopropylether
21. 21
    Otrodried

Procedimiento

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.

Fuente