반응 #678171

반응 방정식

tert-butyl nitrite

methyl 2-amino-5-phenylthiophene-3-carboxylate

→

desired product ( 11b )

수율 100.0%

methyl 5-phenylthiophene-3-carboxylate

수율 100.0%

용매

N,N-dimethylformamide

N,N-dimethylformamide

water

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate (2×20 mL)
2. 2
   세척The organic layer was washed with brine (2×10 mL)
3. 3
   건조dried over sodium sulfate
4. 4
   농축concentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in toluene (5 mL)
6. 6
   농축concentrated in vacuo

실험 절차

To a solution of tert-butyl nitrite (428 μL, 3.6 mmol) in N,N-dimethylformamide (5 mL) at 60° C. was dropwise added a solution of methyl 2-amino-5-phenylthiophene-3-carboxylate (11a) (420 mg, 1.8 mmol) in N,N-dimethylformamide (2.5 mL). The mixture was stirred at 60° C. for 1 hour, poured in water (15 mL) and extracted with ethyl acetate (2×20 mL). The organic layer was washed with brine (2×10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in toluene (5 mL) and concentrated in vacuo to provide the desired product (11b) (390 mg, 1.8 mmol, 99%) which was used without further purification.

출처