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ChemicalBook CAS DataBase List 3-(DIMETHYLAMINO)-1-PHENYL-2-PROPEN-1-ONE
1201-93-0

3-(DIMETHYLAMINO)-1-PHENYL-2-PROPEN-1-ONE synthesis

11synthesis methods
N,N-Dimethylformamide dimethyl acetal

4637-24-5

Acetophenone

98-86-2

3-(DIMETHYLAMINO)-1-PHENYL-2-PROPEN-1-ONE

1201-93-0

In a 100 mL dry round-bottomed flask, acetophenone (1.08 g, 9 mmol) and N,N-dimethylformamide dimethyl acetal (3.9 mL, 30 mmol) were added with 30 mL of xylene as solvent. The reaction mixture was refluxed at 140 °C for 12 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and the heating was stopped after confirming the completion of the reaction. The solvent was removed by distillation under reduced pressure and the resulting crude product was purified by fast column chromatography to afford 3-(dimethylamino)-1-phenyl-2-propen-1-one (1.48 g, 97% yield) as a light yellow solid.

-

Yield:-

Steps:

Multi-step reaction with 2 steps
1.1: sodium methylate / methanol / 0.5 h / 20 °C
1.2: 1 h / 20 °C
2.1: sodium carbonate / ethanol / 2 h / 85 °C

References:

Chen, Jinshan;Properzi, Roberta;Uccello, Daniel P.;Young, Jennifer A.;Dushin, Russell G.;Starr, Jeremy T. [Organic Letters,2014,vol. 16,# 16,p. 4146 - 4149]

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