Reacción #7072

Ecuación de reacción

Triethylene glycol monomethyl ether

triethylamine

cyclopropanecarbonyl chloride

→

title product

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

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturamaintaining the temperature at 0° C. with constant stirring
2. 2
   Otroquenched with saturated ammonium chloride solution
3. 3
   OtroIt was then transferred to a separatory funnel
4. 4
   Lavadowashed with 5% sodium bicarbonate (2×5 ml), 1:1 hydrochloric acid (2×5 ml)
5. 5
   OtroThe dichloromethane layer was separated from the aqueous layer
6. 6
   Secadodried over anhydrous sodium sulphate
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated in vacuo

Procedimiento

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%).

Fuente