Ethyl propiolate → HCID 86652418, Verbindung

HRID 1040402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040402
[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]

Komponenten

7

Edukt 2

HCID 12182Ethyl propiolate2×HCID 108880602-Azidobenzaldehyde

Produkt 2

HCID 86652418HCID 86652418, VerbindungAusbeute 66 %HCID 86652419HCID 86652419, VerbindungAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b8c4a077bec34deb85e99db9cd3bb316
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552220B2

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