Réaction #511492

Équation de réaction

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

8-chloro-1-octanol

tetrahydro-2-furancarboxylic acid

water

→

8-chlorooctyl tetrahydro-2-furancarboxylate

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Extractionextracted with dichloromethane (3×200 ml)
2. 2
   LavageThe combined organic layers were washed with water (2×200 ml)
3. 3
   Séchagedried over magnesium sulphate
4. 4
   Filtrationfiltered
5. 5
   AutreThe solvent removed in vacuum
6. 6
   AutreThe residue (7 g) was purified by column flash chromatography on silica gel

Mode opératoire

A solution of N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (5.7 g) in dichloromethane (100 ml) was slowly added to a solution of 8-chloro-1-octanol (4.1 g), tetrahydro-2-furancarboxylic acid (3.5 g) and 4-dimethylaminopyridine (1.5 g) in dichloromethane (50 ml) at 0° C. The mixture was stirred overnight at room temperature. The resulting solution was then added to water (500 ml) and extracted with dichloromethane (3×200 ml). The combined organic layers were washed with water (2×200 ml), dried over magnesium sulphate and filtered. The solvent removed in vacuum. The residue (7 g) was purified by column flash chromatography on silica gel using toluene/ethyl acetate (90:10) as eluent to give 8-chlorooctyl tetrahydro-2-furancarboxylate.

Source