Quinoline → Ethyl 5-cyano-1-benzothiophene-7-carboxylate

HRID 749430노트

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HRID 749430 반응식
Cl([O-])(=O)(=O)=O.[C:6]([C:8](=[CH:13]N(C)C)[CH:9]=[N+](C)C)#[N:7].[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].N1C2C(=CC=CC=2)C=CC=1.[O-]CC.[Na+]>Cl>[C:6]([C:8]1[CH:13]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]2[S:17][CH:21]=[CH:20][C:19]=2[CH:9]=1)#[N:7]

참가 물질

6

반응물 4

HCID 7047QuinolineHCID 93657Ethyl 2-thienylacetateHCID 2723922Sodium ethoxideHCID 53444588N-[2-cyano-3-(dimethylamino)prop-2-en-1-ylidene]-N-methylmethanaminium perchlorate

생성물 1

HCID 68979189Ethyl 5-cyano-1-benzothiophene-7-carboxylate수율 43%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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온도
0 °C

실험 절차

N-[2-cyano-3-(dimethylamino)prop-2-en-1-ylidene]-N-methylmethanaminium perchlorate (see Collect. Czech. Chem. Commun.; 32; 5; 1967; 1704; 5.84 g, 23.2 mmol) and ethyl 2-thienylacetate (3.95 g, 23.2 mmol) were mixed with quinoline (117 mL) at 0° C. Sodium ethoxide (1.97 g, 27.9 mmol) was added and the mixture was stirred at 0° C. for 30 min and then at room temperature for 15 min. The reaction mixture was heated to 75° C. under nitrogen for 5 h and then cooled to 0° C. Hydrochloric acid (200 mL of 2 M aqueous solution) was added and the mixture extracted thrice with chloroform. The organic solution was washed with brine and then dried over Na2SO4. The solvent was removed by evaporation and the residue flash chromatographed on silica gel (hexane-ethyl acetate, 8:1). There was obtained 2.3 g (43%) of ethyl 5-cyano-1-benzothiophene-7-carboxylate as a pale yellow solid. 1H NMR (300 MHz, CDCl3): 1.5 (t, 3H), 4.5 (qt, 2H), 7.5 (d, 1H), 7.7 (d, 1H), 8.3 (m, 2H).

후처리

  1. waitat room temperature for 15 min
  2. temperatureThe reaction mixture was heated to 75° C. under nitrogen for 5 h
  3. temperaturecooled to 0° C
  4. extractionthe mixture extracted thrice with chloroform
  5. washThe organic solution was washed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed by evaporation
  8. customthe residue flash chromatographed on silica gel (hexane-ethyl acetate, 8:1)

출처 및 근거

ORD 기록
ord-e1b6cdee38834a8092581837ea43ee41
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402581B2

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