Reaktion #4685

Reaktionsgleichung

chloroacetonitrile

sodium hydride

2(R,S)-Cyanomethyl-3-α-naphthylpropionic acid

α-naphthylmethylmalonic acid diethyl ester

→

cyanomethyl-(α-naphthylmethyl)-malonic acid diethyl ester

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated by evaporation in a high vacuum
2. 2
   workup.DISSOLUTIONThe residue is dissolved in ethyl acetate
3. 3
   Waschenwashed with 0.1N hydrochloric acid and water
4. 4
   Trocknendried over sodium sulphate
5. 5
   Einengenconcentrated by evaporation
6. 6
   Sonstigepurified by chromatography on silica gel with toluene

Vorschrift

2(R,S)-Cyanomethyl-3-α-naphthylpropionic acid: 3.0 g of α-naphthylmethylmalonic acid diethyl ester and, after 30 minutes, 0.6 ml of chloroacetonitrile are added to a stirred suspension of 0.44 g of sodium hydride dispersion in 50 ml of DMF. The reaction mixture is stirred for 1 hour at 50° and then concentrated by evaporation in a high vacuum. The residue is dissolved in ethyl acetate, washed with 0.1N hydrochloric acid and water, dried over sodium sulphate, concentrated by evaporation and purified by chromatography on silica gel with toluene, yielding cyanomethyl-(α-naphthylmethyl)-malonic acid diethyl ester.

Quelle