Tert-Butyl nitrite → Methyl 5-phenylthiophene-3-carboxylate

HRID 590989

반응식

HRID 590989 반응식
N(OC(C)(C)C)=O.N[C:9]1[S:10][C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15]>CN(C)C=O.O>[C:18]1([C:11]2[S:10][CH:9]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

5

반응물 2

HCID 10906Tert-Butyl nitriteHCID 705256Methyl 2-amino-5-phenylthiophene-3-carboxylate

생성물 1

HCID 819151Methyl 5-phenylthiophene-3-carboxylate수율 100%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

반응 조건

온도
60 °C

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.

후처리

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. washThe organic layer was washed with brine (2×10 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in toluene (5 mL)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c9133882019c4cfa83115013489f40ff
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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