Methyl propiolate → 2-[5-(methoxycarbonyl)-1H-1,2,3-triazol-1-yl]propanoic acid

HRID 1947755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947755
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].[N:7]([CH:10]([CH3:18])[C:11]([O:13]C(C)(C)C)=[O:12])=[N+:8]=[N-:9]>C1(C)C=CC=CC=1>[CH3:6][O:5][C:1]([C:2]1[N:7]([CH:10]([CH3:18])[C:11]([OH:13])=[O:12])[N:8]=[N:9][CH:3]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 13536Methyl propiolateHCID 86634922Tert-butyl 2-azidopropanate

Produkt 1

HCID 579074512-[5-(methoxycarbonyl)-1H-1,2,3-triazol-1-yl]propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 1.87 g (22.3 mmol) of methyl prop-2-ynoate in 40 mL of toluene was added 1.9 g (11 mmol) of tert-butyl 2-azidopropanate. The reaction mixture was heated at 100° C. for 3 h then cooled to ambient temperature. All volatiles were removed under reduced pressure and the crude residue purified by column chromatography on silica gel eluting with a 5 to 25% acetone in hexanes gradient to afford the title compounds.

Aufarbeitung

  1. temperaturethen cooled to ambient temperature
  2. customAll volatiles were removed under reduced pressure
  3. customthe crude residue purified by column chromatography on silica gel eluting with a 5 to 25% acetone in hexanes gradient

Quellen und Nachweise

ORD-Eintrag
ord-f35f45f9d0334f108b524de85b29de1b
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399480B2

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