Diethyl Ether → (2E)-3-(Dimethylamino)-1-(4-Pyridinyl)-2-Propen-1-One

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Reaction Steps

To 4-acetylpyridine (23 mL) in 350 mL toluene was added 55 mL N,N-dimethylformamide dimethyl acetal. The solution was refluxed for 3 hours and allowed to stir at ambient temperature overnight. An additional 33 mL N,N-dimethylformamide dimethyl acetal of was added. After refluxing for 7 hours, the mixture was concentrated to leave an orange solid. This material was treated with diethyl ether. The resulting yellow solid was collected by vacuum filtration. A total of 25.85 g (71% yield) yellow solid was obtained. 1H NMR (CDCl3) was consistent with the desired structure. LC/MS indicated a single peak with a M+1 molecular ion of m/z 177.1 by positive ESI (electrospray ionization mass spectrometry).

Provenance & Evidence