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

関与物質

役割	名称	HCID	仕込み量
反応物	Hydrochloric Acid	HCID 313	—
反応物	Eugenol	HCID 3314	—
反応物	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
反応物	1-Hydroxybenzotriazole	HCID 75771	—
反応物	Diisopropylethylamine	HCID 81531	—
反応物	(S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid	HCID 641720	—
触媒	4-(Dimethylamino)pyridine	HCID 14284	—
溶媒	Dichloromethane	HCID 6344	—
生成物	(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid 4-allyl-2-methoxy-phenyl ester	HCID 67346743	60%

反応条件

温度	25 °C

反応手順

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%).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08846721B2
出典データセット	uspto-grants-2014_09
ORD ID	ord-bf62190877414805a5b6d6cbbcb353d2
出典メモ	uspto-grants-2014_09