Réaction #5750

Équation de réaction

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

Rendement 75.0%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Extractionthe product was extracted with hexane (20 m1×2)
2. 2
   SéchageThe extract was dried over MgSO4
3. 3
   Autreevaporated in vacuo
4. 4
   Autreto remove the solvent
5. 5
   Autreto give a residue, which

Mode opératoire

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%).

Source