Reaktion #5750

Reaktionsgleichung

water

imidazole

chlorodimethyl t-butylsilane

8-Acetoxy-2,6-dimethyl-2,6-octadien-1-ol

→

1-acetoxy-8-(dimethyl t-butylsilyl)oxy-3,7-dimethyl-2,6-octadiene

Ausbeute 75.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe product was extracted with hexane (20 m1×2)
2. 2
   TrocknenThe extract was dried over MgSO4
3. 3
   Sonstigeevaporated in vacuo
4. 4
   Sonstigeto remove the solvent
5. 5
   Sonstigeto give a residue, which

Vorschrift

8-Acetoxy-2,6-dimethyl-2,6-octadien-1-ol in dimethylformamide (4 ml) was stirred on an ice bath. To the solution were added imidazole (338 mg, 4.96 mmol) and chlorodimethyl t-butylsilane (410 mg, 2.73 mmol), and the mixture was stirred at room temperature for one hour. After addition of water (30 ml) to the reaction mixture, the product was extracted with hexane (20 m1×2). The extract was dried over MgSO4 and evaporated in vacuo to remove the solvent to give a residue, which was subjected to silica gel column chromatography to obtain 1-acetoxy-8-(dimethyl t-butylsilyl)oxy-3,7-dimethyl-2,6-octadiene (606 mg, 75%).

Quelle