Reaktion #11974

Reaktionsgleichung

Trifluoro-acetic acid ethyl ester

1-pyridin-2-yl-ethanone

sodium methoxide

→

4,4,4-trifluoro-1-pyridin-2-yl-butane-1,3-dione

Ausbeute 81.2%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturat reflux overnight
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   ExtraktionThe aqueous solution was extracted with ethyl acetate (10×50 mL)
5. 5
   SonstigeThe organic layers were collected
6. 6
   Trocknendried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   SonstigeThe crude product was purified by column chromatography on silica gel

Vorschrift

Trifluoro-acetic acid ethyl ester (9.82 mL, 82.5 mmol) was added to a solution of 1-pyridin-2-yl-ethanone (5.00 g, 41.2 mmol) in methanol (40 mL) containing sodium methoxide (61.8 mmol). The reaction mixture was heated at reflux overnight, concentrated under reduced pressure and acidified with aqueous hydrochloric acid (10%). The aqueous solution was extracted with ethyl acetate (10×50 mL). The organic layers were collected, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel to give 4,4,4-trifluoro-1-pyridin-2-yl-butane-1,3-dione (7.26 g, 81%).

Quelle