Reacción #5750

Ecuación de reacción

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

Rendimiento 75.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe product was extracted with hexane (20 m1×2)
2. 2
   SecadoThe extract was dried over MgSO4
3. 3
   Otroevaporated in vacuo
4. 4
   Otroto remove the solvent
5. 5
   Otroto give a residue, which

Procedimiento

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%).

Fuente