Réaction #7072

Équation de réaction

Triethylene glycol monomethyl ether

triethylamine

cyclopropanecarbonyl chloride

→

title product

Cyclopropanecarboxylic Acid, 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl Ester

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températuremaintaining the temperature at 0° C. with constant stirring
2. 2
   Autrequenched with saturated ammonium chloride solution
3. 3
   AutreIt was then transferred to a separatory funnel
4. 4
   Lavagewashed with 5% sodium bicarbonate (2×5 ml), 1:1 hydrochloric acid (2×5 ml)
5. 5
   AutreThe dichloromethane layer was separated from the aqueous layer
6. 6
   Séchagedried over anhydrous sodium sulphate
7. 7
   Filtrationfiltered
8. 8
   Autreevaporated in vacuo

Mode opératoire

Triethylene glycol monomethyl ether (1.1 eq, 5.26 mmol, 0.84 ml), triethylamine (1.1 eq, 5.26 mmol, 0.73 ml) was taken in a 10 ml round bottom flask and dichloromethane (3 ml) was added. This mixture was cooled to 0° C. and then cyclopropanecarbonyl chloride (4.78 mmol, 0.5 g, 0.43 ml) was added in a dropwise fashion maintaining the temperature at 0° C. with constant stirring. A yellowish-orange solid was observed after some time. Stirring was continued for 1 hr at 0° C. The reaction was monitored by thin layer chromatography, and then quenched with saturated ammonium chloride solution. It was then transferred to a separatory funnel, washed with 5% sodium bicarbonate (2×5 ml), 1:1 hydrochloric acid (2×5 ml) and then with brine (5 ml). The dichloromethane layer was separated from the aqueous layer, dried over anhydrous sodium sulphate, filtered, and evaporated in vacuo to give the title product as a pale yellow liquid. Purification was attempted by flash chromatography and vacuum distillation (b.p.=144° C., 3.0 mm of Hg) which afforded the pure product as a colorless liquid (527.0 mg, 48%).

Source