(Trimethylsilyl)imidazole → HCID 57709215, Verbindung

HRID 546823

Reaktionsgleichung

Reaktionsgleichung von HRID 546823
[CH3:1][Si:2]([CH3:9])([CH3:8])N1C=CN=C1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([CH3:19])([O:20][Si:2]([CH3:1])([CH3:8])[CH3:9])[CH3:18])=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 28925(Trimethylsilyl)imidazoleHCID 516892Sodium BicarbonateHCID 126819202-(4-Bromophenyl)propan-2-ol

Produkt 1

HCID 57709215HCID 57709215, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-trimethylsilylimidazole (80.6 mL, 0.552 mol) was added to a solution of the crude 2-(4-bromo-phenyl)-propan-2-ol in tetrahydrofuran (500 mL) in a nitrogen atmosphere at room temperature, and the mixture was stirred at the same temperature overnight. The reaction mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel chromatography (n-hexane:ethyl acetate=40:1) to give the title compound as a colorless oil (125.6 g, 87% in two steps).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8cd1086b1c9341fca47e010f3347dc7a
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

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