反応 #7072

反応方程式

Triethylene glycol monomethyl ether

triethylamine

cyclopropanecarbonyl chloride

→

title product

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

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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%).

出典