Reacción #2045041

Ecuación de reacción

1,3-dicyclohexylcarbodiimide

4-nitrophenoxyacetic acid-2-hydroxyethyl ester

(4-Nitro-phenoxy)-acetic acid-2-hydroxy-ethyl ester

2-(4-nitrophenoxy)propionic acid

2-(4-Nitro-phenoxy)-propionic acid

→

55

Rendimiento 29.8%

2-(4-Nitro-phenoxy)-propionic acid 2-[2-(4-nitro-phenoxy)-acetoxy]-ethyl ester

Rendimiento 29.8%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe solids were filtered off
2. 2
   workup.DISTILLATIONdichloromethane distilled off
3. 3
   Otroto get crude 55
4. 4
   OtroThe crude 55 was purified by column chromatography on silica gel

Procedimiento

To a mixture of 4-nitrophenoxyacetic acid-2-hydroxyethyl ester 41 (100 g, 410 mmol) and 2-(4-nitrophenoxy)propionic acid 47 (95 g, 450 mmol) in anhydrous dichloromethane (1000 ml) under nitrogen atm. was added a solution of 1,3-dicyclohexylcarbodiimide (240 g, 1160 mmol) in anhydrous dichloromethane (600 ml) dropwise. The reaction mixture was stirred at room temperature for 12 hrs. The solids were filtered off and dichloromethane distilled off to get crude 55. The crude 55 was purified by column chromatography on silica gel using benzene as eluant to give pure 55 (53 g, 29%) as a yellow low melting solid.

Fuente