Reaktion #5752

Reaktionsgleichung

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

Ausbeute 102.7%

Lösungsmittel

methylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   ExtraktionThe product was extracted with ether (20 m1×2)
3. 3
   TrocknenThe extract was dried over Na2SO4
4. 4
   Einengenconcentrated
5. 5
   Sonstigeto give a residue, which
6. 6
   Sonstigewas then purified with silica gel column chromatography

Vorschrift

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%).

Quelle