Imidazole → (5-Chloro-1-pentyloxy)(2,2-dimethylethyl)dimethylsilane

HRID 1789542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789542
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[Si:8](Cl)([C:11](C)(C)C)([CH3:10])[CH3:9].[CH3:16]N(C)C=O.N1[CH:25]=[CH:24]N=C1>O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][Si:8]([CH2:11][CH:24]([CH3:25])[CH3:16])([CH3:10])[CH3:9]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 789155-Chloro-1-pentanol

Produkt 1

HCID 20028701(5-Chloro-1-pentyloxy)(2,2-dimethylethyl)dimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

5-Chloropentanol (325 g, 2.65 moles) is added to a solution containing tert-butyldimethylsilyl chloride (439 g, 2.91 moles) and dimethylformamide (1.625 liters). The solution is stirred and imidazole (199 g, 2.91 moles) is added at once. The solution is stirred at room temperature for 6 hours, after which time water (1 liter) is added and the reaction is partitioned with hexanes. The organic phase is separated and the solvent volume reduced under vacuum. The residue is dried over anhydrous magnesium sulfate and the remaining solvent removed under vacuum, leaving a clear, colorless oil. The crude product is subsequently fractionally distilled under reduced pressure leaving the product as a clear, colorless oil (534 g, 2.26 moles), BP 71° C./0.3 mm.

Aufarbeitung

  1. stirringThe solution is stirred at room temperature for 6 hours
  2. customthe reaction is partitioned with hexanes
  3. customThe organic phase is separated
  4. dry with materialThe residue is dried over anhydrous magnesium sulfate
  5. customthe remaining solvent removed under vacuum
  6. customleaving a clear, colorless oil
  7. distillationThe crude product is subsequently fractionally distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-642222c817f14c568dd170c84ef8109c
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04689345

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