Reacción #2460303

Ecuación de reacción

1,3-dicyclohexyl-carbodiimide

thioxanthen-9-one-2-carboxylic acid

2-hydroxyethylmethacrylate

4-dimethylamino-pyridine p-toluenesulfonic acid salt

→

pale yellow solid

Rendimiento 17.0%

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

Rendimiento 17.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was warmed to ambient and
2. 2
   FiltraciónThe precipitated urea by product was filtered
3. 3
   Lavadothe filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe product was purified by column chromatography

Procedimiento

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).

Fuente