Stannane, tributyl(1-ethoxyethenyl)- → Methyl 2-(1-ethoxyvinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 1409390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1409390
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](Br)[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=1)=[O:4].C([Sn](CCCC)(CCCC)[C:24]([O:26][CH2:27][CH3:28])=[CH2:25])CCC>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:27]([O:26][C:24]([C:7]1[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[N:6]=1)=[CH2:25])[CH3:28]

Komponenten

6

Edukt 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 58638548Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Produkt 1

HCID 86714651Methyl 2-(1-ethoxyvinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (10 g, 29.9 mmol) was dissolved in dioxane (200 ml). Tributyl(1-ethoxy-vinyl)stannane (16.2 g, 44.8 mmol) was added to the solution. The resulting mixture was degassed and purged with argon for 20 min. Then Pd(PPh3)4 (3.45 g, 2.99 mmol) was added and the mixture was refluxed overnight. The reaction mixture was cooled to RT and diluted with cold water. The mixture was extracted with EtOAc and washed with aqueous KF solution. The organic layer was concentrated to give the desired product. Yield 12.1 g. LC-MS: [M+1]=327.78.

Aufarbeitung

  1. customThe resulting mixture was degassed
  2. custompurged with argon for 20 min
  3. temperaturethe mixture was refluxed overnight
  4. extractionThe mixture was extracted with EtOAc
  5. washwashed with aqueous KF solution
  6. concentrationThe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-30a2ec426d9c4cd7af05a8609c857d29
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921378B2

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