Réaction #5753

Équation de réaction

water

methyl 2-acetyl-10-(dimethyl t-butylsilyl)oxy-5,9-dimethyl-4,8-decadienate

sodium iodide

water

→

6,10-dimethyl-11-(dimethyl t-butylsilyl)oxy-5,9-undecadien-2-one

Rendement 70.2%

Solvants

hexamethylphosphoric triamide

Conditions de réaction

Traitement

1. 1
   Températureto cool to room temperature
2. 2
   ExtractionThe product was extracted with ether (5 m1×2)
3. 3
   SéchageThe extract was dried over Na2SO4
4. 4
   Concentrationconcentrated
5. 5
   Autreto give a residue, which
6. 6
   Autrewas then purified with silica gel column chromatography

Mode opératoire

To a solution of methyl 2-acetyl-10-(dimethyl t-butylsilyl)oxy-5,9-dimethyl-4,8-decadienate (96 mg, 0.25 mmol) in hexamethylphosphoric triamide (0.5 ml) were added sodium iodide (45 mg, 0.30 mmol) and water (0.01 ml), and the mixture was stirred at 150° C. After two hours, the reaction mixture was allowed to cool to room temperature, and water (2 ml) was added thereto. The product was extracted with ether (5 m1×2). The extract was dried over Na2SO4, and concentrated to give a residue, which was then purified with silica gel column chromatography to obtain 6,10-dimethyl-11-(dimethyl t-butylsilyl)oxy-5,9-undecadien-2-one (57 mg, 70%).

Source