Réaction #5752

Équation de réaction

water

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

sodium chloride

water

→

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

Rendement 102.7%

Solvants

methylsulfoxide

Conditions de réaction

Traitement

1. 1
   Températureto cool to room temperature
2. 2
   ExtractionThe product was extracted with ether (20 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-5,9-dimethyl-10-(methoxymethyl)oxy-4,8-decadienate (420 mg, 1.37 mmol) in methylsulfoxide (4 ml) were added sodium chloride (160 mg, 2.74 mmol) and water (0.1 ml), and the mixture was stirred at 150° C. After five hours, the reaction mixture was allowed to cool to room temperature, and water (10 ml) was added thereto. The product was extracted with ether (20 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-(methoxymethyl)oxy- 5,9-undecadien-2-one (358 mg, 67%).

Source