Reaktion #5751

Reaktionsgleichung

water

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

sodium chloride

water

→

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

Ausbeute 70.0%

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-(2-tetrahydropyranyl)oxy-4,8-decadienate (370 mg, 1.05 mmol) in methylsulfoxide (2 ml) were added sodium chloride (180 mg, 3.08 mmol)and water (0.1 ml), and the mixture was stirred at 150° C. After four hours, the reaction mixture was allowed to cool to room temperature, and water (15 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-(2-tetrahydropyranyl)oxy-5,9-undecadien-2-one (70%).

Quelle