Reacción #74187

Ecuación de reacción

HCl

pyridine

bicyclo[3.2.1]octane-2,4-dione

chloroacetyl chloride

→

chloro-acetic acid 4-oxo-bicyclo[3.2.1]oct-2-en-2-yl ester

Rendimiento 86.7%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate (2×100 ml)
2. 2
   SecadoThe combined organic extracts are dried over magnesium sulphate
3. 3
   Filtraciónfiltered
4. 4
   Otroevaporated under reduced pressure
5. 5
   Otroto give an orange oil
6. 6
   workup.DISTILLATIONThe crude product is distilled under reduced pressure

Procedimiento

Into a 250 ml round bottom flask containing the bicyclo[3.2.1]octane-2,4-dione (10 g, 72 mmol) is added dry dichloromethane (100 ml) and pyridine (6.28 g, 87 mmol). To the stirred mixture is added dropwise over a period of 15 minutes the chloroacetyl chloride (9.82 g, 72 mmol) diluted in dichloromethane (100 ml). The reaction mixture is therefore stirred for 2 hours at room temperature. The reaction mixture is therefore poured into 100 ml of aqueous 2N HCl and extracted with ethyl acetate (2×100 ml). The combined organic extracts are dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an orange oil. The crude product is distilled under reduced pressure to give chloro-acetic acid 4-oxo-bicyclo[3.2.1]oct-2-en-2-yl ester (13.4 g).

Fuente