Reacción #59980

Ecuación de reacción

water

methyl 2-cyclopentanonecarboxylate

ethylene glycol

benzene

→

title compound

Rendimiento 70.3%

Methyl1,4-dioxaspiro[4.4]nonan-6-carboxylate

Rendimiento 70.3%

Disolventes

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroseparator was attached to a round bottom flask
2. 2
   TemperaturaThe mixture was heated
3. 3
   Temperaturaunder reflux for 2 hours
4. 4
   Concentraciónthe mixture was concentrated
5. 5
   Otropurified by silica gel column chromatography (elution solvent: ethyl acetate/heptane=1/9, 1/1)

Procedimiento

A reflux condenser equipped with a Dean-Stark water separator was attached to a round bottom flask containing methyl 2-cyclopentanonecarboxylate (2 ml, 16.2 mmol), ethylene glycol (994 μl, 17.8 mmol), p-toluenesulfonic acid monohydrate (139 mg, 0.73 mmol), and benzene (30 ml). The mixture was heated under reflux for 2 hours. To the reaction mixture, triethylamine (0.22 ml) was added and the mixture was concentrated and purified by silica gel column chromatography (elution solvent: ethyl acetate/heptane=1/9, 1/1) to obtain the title compound (2.12 g, yield 70.3%) as a colorless oil.

Fuente