3-Phenylprop-2-Enal → N,N-diethyl-7-phenyl-5-hydroxy-3-oxo-6-heptenamide

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Reaction Conditions

Reaction Steps

2.65 cm3 of diisopropylamine are introduced into a three-necked, round-bottomed flask equipped with a septum and a dropping funnel and are then cooled to -10° C. 10.4 cm3 of n-butyllithium in solution in hexane at 1.6 mol/liter (16.6 mmol) are then slowly added and the mixture is then stirred for 15 minutes. 1.40 g of N,N-diethylacetoacetamide (8.65 mmol) are then slowly added and the mixture is then stirred for 15 minutes. 1.0 g of cinnamaldehyde (7.57 mmol) is added. The mixture is stirred for 25 minutes and then 2 cm3 of concentrated hydrochloric acid and 25 cm3 of water are added. Extraction is carried out with 2 times 25 cm3 of dichloromethane. The combined organic phases are washed with 4 times 50 cm3 of water and dried over sodium sulphate. After filtration and concentration to dryness, there is obtained, with a yield of 85%, 1.86 g of N,N-diethyl-7-phenyl-5-hydroxy-3-oxo-6-heptenamide, the structure of which is confirmed by the proton nuclear magnetic resonance spectrum.

Provenance & Evidence