Reacción #468489

Ecuación de reacción

water

hexane

ethyl acetate

1.3-benzodioxole

aluminum

→

subtitle compound

Benzo(1.3)dioxol-5-yl-oxo-acetic acid ethyl ester

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothe organic layer was washed with further volumes of water (3×500 ml), saturated sodium bicarbonate solution (500 ml) and brine (500 ml)
2. 2
   SecadoThe organic layer was dried (magnesium sulphate)
3. 3
   Concentraciónconcentrated
4. 4
   Otroto give an orange oil

Procedimiento

A mixture of ethyl oxalyl chloride (50 ml, 0.45 mmol) and 1.3-benzodioxole (50 g, 0.41 mmol) in dichloromethane (40 ml) was added dropwise to a stirred slurry of aluminum thichloride (71 g, 0.53 mmol) in dichloromethane (500 ml) at 0° C. under a nitrogen atmosphere. After 2 hours the mixture was poured into iced water and the organic layer was washed with further volumes of water (3×500 ml), saturated sodium bicarbonate solution (500 ml) and brine (500 ml). The organic layer was dried (magnesium sulphate) and concentrated to give an orange oil. Flash column chromatography (90% hexane, 10% ethyl acetate) gave 30 g of the subtitle compound as a pale yellow oil.

Fuente