反应 #7072

反应方程式

Triethylene glycol monomethyl ether

triethylamine

cyclopropanecarbonyl chloride

→

title product

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

溶剂

dichloromethane

反应条件

后处理

1. 1
   温度maintaining the temperature at 0° C. with constant stirring
2. 2
   其他quenched with saturated ammonium chloride solution
3. 3
   其他It was then transferred to a separatory funnel
4. 4
   洗涤washed with 5% sodium bicarbonate (2×5 ml), 1:1 hydrochloric acid (2×5 ml)
5. 5
   其他The dichloromethane layer was separated from the aqueous layer
6. 6
   干燥dried over anhydrous sodium sulphate
7. 7
   过滤filtered
8. 8
   其他evaporated in vacuo

实验过程

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%).

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