Reaktion #11658

Reaktionsgleichung

(4-Nitro-phenyl)-acetic acid

morpholine

sodium bicarbonate

→

1-morpholin-4-yl-2-(4-nitro-phenyl)-ethanone

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA room temperature solution of 1.8839 gms
2. 2
   Temperaturto cool to room temperature
3. 3
   ExtraktionThe resulting mixture is extracted with ethyl acetate
4. 4
   ExtraktionThe aqueous layer is re-extracted four more times with ethyl acetate
5. 5
   SonstigeThe combined organics are evaporated to dryness in vacuo
6. 6
   SonstigeThe crude product residue is then chromatographed by flash silica gel chromatography
7. 7
   Sonstigeevaporation of solvent

Vorschrift

A room temperature solution of 1.8839 gms. (4-Nitro-phenyl)-acetic acid in tetrahydrofuran (5 mL) is treated with 1.8069 gms. 1′,1′-carbonyl-diimidizole. The reaction mixture is stirred for 1 h. The reaction mixture is then treated with 1.0 mL morpholine. The reaction is heated overnight at 35° C. The reaction is then allowed to cool to room temperature, and is made basic with the addition of saturated aqueous sodium bicarbonate. The resulting mixture is extracted with ethyl acetate. The aqueous layer is re-extracted four more times with ethyl acetate. The combined organics are evaporated to dryness in vacuo. The crude product residue is then chromatographed by flash silica gel chromatography using 60% ethyl acetate in hexanes as the eluant. Following evaporation of solvent, 1-morpholin-4-yl-2-(4-nitro-phenyl)-ethanone is isolated as a white solid in the amount of 1.4009 gms.

Quelle