Imidazole → ((1-(4-Bromophenyl)hexyl)oxy)(tert-butyl)dimethylsilane

HRID 606544

Reaktionsgleichung

Reaktionsgleichung von HRID 606544
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([OH:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][CH:11]=1.N1C=CN=C1>CN(C=O)C.CCOCC>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]([O:22][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:14][CH:15]=1

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 126030861-(4-Bromophenyl)hexan-1-ol

Produkt 1

HCID 57438973((1-(4-Bromophenyl)hexyl)oxy)(tert-butyl)dimethylsilaneAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

t-Butyidimethylsilylchloride (2.49 g, 16.5 mmol) was added to a solution of the alcohol 6 (3.6 g, 14.0 mmol) and imidazole (1.91 g, 28.0 mmol) in DMF (22 mL) at 23° C. The reaction was stirred for 16 h, diluted with Et2O and washed with 1 N HCl, saturated aqueous NaHCO3 and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 100% hex) afforded 5.18 g (63%) of the silyl ether 7 as a clear, colorless oil.

Aufarbeitung

  1. washwashed with 1 N HCl, saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fcfdca2a10de4bdfbb3309c0b99e2259
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915316B2

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