Réaction #170988

Équation de réaction

1,3-dicyclohexyl carbodiimide

[4-nitrophenoxy]-acetic acid-2-hydroxyethyl ester

(4-Nitrophenoxy)-acetic acid-2-hydroxy-ethyl ester

2-(4-nitrophenoxy)-propionic acid

2-(4-Nitrophenoxy)-propionic acid

→

38

Rendement 29.8%

2-(4-Nitrophenoxy)-propionic acid 2-[2-(4-nitrophenoxy)-acetoxy]-ethyl ester

Rendement 29.8%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   FiltrationThe solids were filtered off
2. 2
   workup.DISTILLATIONdichloromethane distilled off
3. 3
   Autreto get crude 38
4. 4
   AutreThe crude 38 was purified by column chromatography on silica gel

Mode opératoire

To a mixture of [4-nitrophenoxy]-acetic acid-2-hydroxyethyl ester 23 (100 grams, 410 mmol) and 2-(4-nitrophenoxy)-propionic acid 29 (95 g, 450 mmol) in anhydrous dichloromethane (1000 ml) under nitrogen atmosphere was added dropwise a solution of 1,3-dicyclohexyl carbodiimide (240 g, 1160 mmol) in anhydrous dichloromethane (600 ml). The reaction mixture was stirred at room temperature for 12 hrs. The solids were filtered off and dichloromethane distilled off to get crude 38. The crude 38 was purified by column chromatography on silica gel using benzene as eluant to give pure 38 (53 grams, 29%) as a yellow low melting solid.

Source