(Trimethylsilyl)imidazole → [1-(3-Bromo-phenyl)-1-ethyl-propoxy]-trimethyl-silane

HRID 546829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546829
[CH3:1][Si:2]([CH3:9])([CH3:8])N1C=CN=C1.[Br:10][C:11]1[CH:12]=[C:13]([C:17]([OH:22])([CH2:20][CH3:21])[CH2:18][CH3:19])[CH:14]=[CH:15][CH:16]=1>O1CCCC1>[Br:10][C:11]1[CH:12]=[C:13]([C:17]([CH2:18][CH3:19])([O:22][Si:2]([CH3:1])([CH3:8])[CH3:9])[CH2:20][CH3:21])[CH:14]=[CH:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 28925(Trimethylsilyl)imidazoleHCID 574434823-(3-Bromophenyl)pentan-3-ol

Produkt 1

HCID 57709150[1-(3-Bromo-phenyl)-1-ethyl-propoxy]-trimethyl-silaneAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-trimethylsilylimidazole (8.2 mL, 55.81 mol) was added to a solution of the crude 3-(3-bromo-phenyl)-pentan-3-ol in tetrahydrofuran (100 mL) in a nitrogen atmosphere at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into distilled water, followed by extraction with dichloromethane. The extract was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel chromatography (n-hexane:ethyl acetate=40:1) to give the title compound as a colorless oil (8.7 g, 59% in two steps).

Aufarbeitung

  1. additionThe reaction mixture was poured
  2. distillationinto distilled water
  3. extractionfollowed by extraction with dichloromethane
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-544cf9b858404d80848f9f6f4473e1c7
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

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