Réaction #74187

Équation de réaction

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

Rendement 86.7%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate (2×100 ml)
2. 2
   SéchageThe combined organic extracts are dried over magnesium sulphate
3. 3
   Filtrationfiltered
4. 4
   Autreevaporated under reduced pressure
5. 5
   Autreto give an orange oil
6. 6
   workup.DISTILLATIONThe crude product is distilled under reduced pressure

Mode opératoire

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).

Source