تفاعل #2045036

ord-0af188352fa74b4c9f2640191ddffd22

معادلة التفاعل

C(=NC1CCCCC1)=NC1CCCCC1
1,3-dicyclohexyl carbodiimide
CC(Oc1ccc([N+](=O)[O-])cc1)C(=O)O
2-(4-nitrophenoxy) propionic acid
CC(Oc1ccc([N+](=O)[O-])cc1)C(=O)O
2-(4-Nitro-phenoxy)-propionic acid
CC(Oc1ccc([N+](=O)[O-])cc1)C(=O)OCCO
2-(4-nitrophenoxy)propionic acid 2-hydroxyethyl ester
CC(Oc1ccc([N+](=O)[O-])cc1)C(=O)OCCO
2-(4-Nitro-phenoxy)-propionic acid 2-hydroxy-ethyl ester
CC(Oc1ccc([N+](=O)[O-])cc1)C(=O)OCCOC(=O)C(C)Oc1ccc([N+](=O)[O-])cc1
49
المردود 35.1%
CC(Oc1ccc([N+](=O)[O-])cc1)C(=O)OCCOC(=O)C(C)Oc1ccc([N+](=O)[O-])cc1
2-(4-Nitrophenoxy)propionic acid 2-[2-(4-nitrophenoxy)propionyloxy]ethyl ester
المردود 35.1%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحThe solids were filtered off
  2. 2
    workup.DISTILLATIONdichloromethane distilled off
  3. 3
    أخرىto get crude 49
  4. 4
    أخرىThe crude 49 was purified by column chromatography on silica gel

الإجراء التجريبي

To a mixture of 2-(4-nitrophenoxy) propionic acid 47 (25 grams, 118.5 mmol) and 2-(4-nitrophenoxy)propionic acid 2-hydroxyethyl ester 48 (25 grams, 108 mmol) in anhydrous dichloromethane (625 ml) under nitrogen atm. was added dropwise a solution of 1,3-dicyclohexyl carbodiimide (40 g, 194 mmol) in anhydrous dichloromethane (250 ml). The reaction mixture was stirred at room temperature for 8 hours. The solids were filtered off and dichloromethane distilled off to get crude 49. The crude 49 was purified by column chromatography on silica gel using hexane as eluant to get pure 49 (17 g, 35.1%) as a white powder.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08409559B2uspto-grants-2013_04