Ethyl propiolate → HCID 86652418, 화합물

HRID 1040402노트

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HRID 1040402 반응식
[N:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])=[N+:2]=[N-:3].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[C:13]#[CH:14]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[CH:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N:1]1[CH:14]=[C:13]([C:12]([O:16][CH2:17][CH3:18])=[O:15])[N:3]=[N:2]1)=[O:7].[CH:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N:1]1[C:13]([C:12]([O:16][CH2:17][CH3:18])=[O:15])=[CH:14][N:3]=[N:2]1)=[O:7]

참가 물질

7

반응물 2

HCID 12182Ethyl propiolate2회HCID 108880602-Azidobenzaldehyde

생성물 2

HCID 86652418HCID 86652418, 화합물수율 66%HCID 86652419HCID 86652419, 화합물수율 17%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To a solution of 2-azidobenzaldehyde (100 mg, 0.68 mmol) in 1.0 mL of dry N,N-dimethylformamide was added ethyl propiolate (0.14 mL, 1.4 mmol) at room temperature. After being stirred at 100° C. for 12 h, ethyl propiolate (0.14 mL, 1.4 mmol) was added again with additional stirring for 12 h. After cooling, the reaction mixture was diluted with a 5:1 solution (12 mL) of ethyl acetate and hexane. The solution was washed with water twice, brine, and dried over Na2SO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25) to obtain ethyl 1-(2-formylphenyl)-1H-1,2,3-triazol-4-carboxylate as a crystal (111 mg, 66%) and ethyl 1-(2-formylphenyl)-1H-1,2,3-triazol-5-carboxylate as a oil (28 mg, 17%).

후처리

  1. stirringwith additional stirring for 12 h
  2. temperatureAfter cooling
  3. washThe solution was washed with water twice
  4. dry with materialbrine, and dried over Na2SO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25)

출처 및 근거

ORD 기록
ord-b8c4a077bec34deb85e99db9cd3bb316
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552220B2

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