Reaction #1447097

Reaction equation

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

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThe cooling bath is removed
2. 2
   workup.ADDITIONThen, 1 M aqueous NaOH solution (8.5 mL) is added
3. 3
   Concentrationthe resulting solution is concentrated under reduced pressure
4. 4
   workup.ADDITIONWater is added to the residue
5. 5
   Extractionthe resulting mixture is extracted with ethyl acetate
6. 6
   WashThe combined organic extracts are washed with brine
7. 7
   Dryingdried (Na2SO4)
8. 8
   Concentrationconcentrated
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
    Otheron crushed ice
13. 13
    ExtractionThe resultant mixture is extracted twice with ethyl acetate
14. 14
    WashThe combined extracts are washed with brine
15. 15
    Dryingdried (sodium sulphate)
16. 16
    Concentrationconcentrated under reduced pressure
17. 17
    workup.ADDITIONThe residue is treated with methanol
18. 18
    Otherthe precipitate formed
19. 19
    Otheris separated
20. 20
    WashThe precipitate is then washed with diisopropylether
21. 21
    Otherdried

Procedure

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.

Source