Imidazole → [1-(4-Bromophenyl)ethoxy](tert-butyl)dimethylsilane

HRID 63660

Reaktionsgleichung

Reaktionsgleichung von HRID 63660
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1.N1C=CN=C1.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][Si:20]([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21])[CH3:9])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 953521-(4-Bromophenyl)ethanol

Produkt 1

HCID 18516082[1-(4-Bromophenyl)ethoxy](tert-butyl)dimethylsilaneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-bromophenyl)ethan-1-ol (2.8 g, 13.93 mmol) and imidazole (2.84 g, 41.79 mmol) in DMF (35 mL) was added TBDMSCl (4.18 g, 27.86 mmol) at r.t., and the reaction was stirred overnight. The reaction was diluted with water (70 mL) and extracted with EtOAc (50 mL×3). Organics were washed with brine (50 mL), dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography (PE:EtOAc=100:1) to give 4.08 g (95%) of the title compound as a colorless oil.

Aufarbeitung

  1. extractionextracted with EtOAc (50 mL×3)
  2. washOrganics were washed with brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (PE:EtOAc=100:1)

Quellen und Nachweise

ORD-Eintrag
ord-a13da35d033741eab7a1d27a09534e00
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447046B2

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