反応 #2460303

反応方程式

1,3-dicyclohexyl-carbodiimide

thioxanthen-9-one-2-carboxylic acid

2-hydroxyethylmethacrylate

4-dimethylamino-pyridine p-toluenesulfonic acid salt

→

pale yellow solid

収率 17.0%

(2-methacryloxyethyl)thioxanthen-9-one-2-carboxylate

収率 17.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   温度the reaction mixture was warmed to ambient and
2. 2
   ろ過The precipitated urea by product was filtered
3. 3
   洗浄the filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine
4. 4
   濃縮concentrated
5. 5
   その他The product was purified by column chromatography

実験手順

A mixture of thioxanthen-9-one-2-carboxylic acid (3.8 g, 19.8 mmol), 2-hydroxyethylmethacrylate (7.7 g, 59.3mmol), 4-dimethylamino-pyridine p-toluenesulfonic acid salt (2.3 g, 7.9mmol), and anhydrous dichloromethane (31 mL) is cooled to 0° C. under nitrogen and treated with 1,3-dicyclohexyl-carbodiimide (2.1 g, 10.1 mmol). After 15 min, the reaction mixture was warmed to ambient and stirred for 12 h. The precipitated urea by product was filtered, and the filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine. The solution was dried (Na2SO4)and concentrated to deposit yellow oil. The product was purified by column chromatography to provide 500 mg of a pale yellow solid (17% of theory). 1H (CDCl3): δ 1.99 (s, 3H), 4.60 (dd, 4H), 5.60 (s, 1H), 6.20 (s, 1H), 7.60 (m, 4H), 8.20 (d, 1H), 8.70 (d, 1H), 9.30 (s, 1H).

出典