تفاعل #1447097

معادلة التفاعل

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

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe cooling bath is removed
2. 2
   workup.ADDITIONThen, 1 M aqueous NaOH solution (8.5 mL) is added
3. 3
   تركيزthe resulting solution is concentrated under reduced pressure
4. 4
   workup.ADDITIONWater is added to the residue
5. 5
   استخلاصthe resulting mixture is extracted with ethyl acetate
6. 6
   غسيلThe combined organic extracts are washed with brine
7. 7
   تجفيفdried (Na2SO4)
8. 8
   تركيزconcentrated
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
    أخرىon crushed ice
13. 13
    استخلاصThe resultant mixture is extracted twice with ethyl acetate
14. 14
    غسيلThe combined extracts are washed with brine
15. 15
    تجفيفdried (sodium sulphate)
16. 16
    تركيزconcentrated under reduced pressure
17. 17
    workup.ADDITIONThe residue is treated with methanol
18. 18
    أخرىthe precipitate formed
19. 19
    أخرىis separated
20. 20
    غسيلThe precipitate is then washed with diisopropylether
21. 21
    أخرىdried

الإجراء التجريبي

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.

المصدر