反応 #169666

反応方程式

eugenol

HCl

HOBt

((S)-2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid

N-ethyldiisopropyl amine

EDCI

→

solid

収率 60.0%

(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid 4-allyl-2-methoxy-phenyl ester

収率 60.0%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   洗浄washed with water (4×100 mL)
2. 2
   乾燥dried (Na2SO4)
3. 3
   濃縮concentrated
4. 4
   その他The crude product obtained
5. 5
   その他was further purified by column chromatography

実験手順

To a solution of ((S)-2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid (2.1 g, 12.0 mmol) in dichloromethane were added N-ethyldiisopropyl amine (10.3 mL), EDCI. HCl (6.9 g, 36.0 mmol), HOBt (1.8 g, 12.0 mmol), DMAP (0.14 g, 1.2 mmol) at ice temperature (0° C.) and the reaction mixture was stirred at same temperature over a period of 15 min. Then eugenol (2.18 g, 13.2 mmol) was added to the reaction mixture at same temperature and the mixture was stirred at room temperature (25° C.) over a period of 12 h. The resulting mixture was diluted with dichloromethane (200 mL), washed with water (4×100 mL), dried (Na2SO4) and concentrated. The crude product obtained was further purified by column chromatography to obtain colourless solid (2.3 g, 60%).

出典