تفاعل #442870

معادلة التفاعل

ethyl bromoacetate

ethyl 7-nitro-1H-indole-2-carboxylate

sodium hydride

→

ethyl 1-ethoxycarbonylmethyl-7-nitro-1H-indole-2-carboxylate

المردود 78.0%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe resulting mixture was stirred at 50°-60° C. for 4 hours
2. 2
   درجة الحرارةThe reaction mixture was cooled to room temperature
3. 3
   استخلاصfollowed by extraction with ethyl acetate (three times)
4. 4
   غسيلThe organic layer was washed with water
5. 5
   تجفيفdried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
7. 7
   أخرىthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95)

الإجراء التجريبي

To a solution of ethyl 7-nitro-1H-indole-2-carboxylate (2.00 g, 8.45 mmol) in N,N-dimethylformamide (50 ml) was added 60% sodium hydride (0.34 g, 8.54 mmol), and the reaction mixture was stirred at room temperature until it became transparent. Then, ethyl bromoacetate (1.43 g, 8.54 mmol) was added and the resulting mixture was stirred at 50°-60° C. for 4 hours. The reaction mixture was cooled to room temperature and poured into ice water, followed by extraction with ethyl acetate (three times). The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95) to obtain ethyl 1-ethoxycarbonylmethyl-7-nitro-1H-indole-2-carboxylate (2.11 g).

المصدر