Reacción #1794954

Ecuación de reacción

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

Rendimiento 70.0%

Disolventes

methylsulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool to room temperature
2. 2
   ExtracciónThe product was extracted with ether (20 mlx2)
3. 3
   SecadoThe extract was dried over Na2SO4
4. 4
   Concentraciónconcentrated
5. 5
   Otroto give a residue, which
6. 6
   Otrowas then purified with silica gel column chromatography

Procedimiento

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 mlx2). 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%). IR(film)cm-1 ; 2950, 2880, 1720, 1442, 1358, 1120, 1078, 1024, 905, 870, 815.

Fuente