反応 #169676

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

→

product

収率 64.3%

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

収率 64.3%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   洗浄washed with water (4×500 mL)
2. 2
   乾燥dried (Na2SO4)
3. 3
   濃縮concentrated
4. 4
   その他The residue obtained upon evaporation of the solvent
5. 5
   洗浄was washed with petroleum ether

実験手順

To a solution of ((S)-2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid (30.0 g, 0.17 mol) in dichloromethane (300 mL) were added N-ethyldiisopropyl amine (147 mL, 0.86 mol), EDCI. HCl (98.0 g, 0.51 mol), HOBt (13.1 g, 0.08 mol), DMAP (0.2 g, 0.01 mol) at ice temperature (0° C.) and the reaction mixture was stirred at same temperature over a period of 15 min. Then eugenol (26.1 mL, 0.17 mol) was added to the reaction mixture at same temperature and the mixture was stirred at room temperature (25° C.) over a period of 5 h. The resulting mixture was diluted with dichloromethane (2.0 L), washed with water (4×500 mL), dried (Na2SO4) and concentrated. The residue obtained upon evaporation of the solvent was washed with petroleum ether to obtain product as a off-white solid (35.0 g, 63%).

出典