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

HRID 590989

反応式

HRID 590989 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 819151Methyl 5-phenylthiophene-3-carboxylate収率 100%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c9133882019c4cfa83115013489f40ff
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

関連ノート

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