Ethyl Acetoacetate → HCID 59487381, compound

Participants

Reaction Conditions

Reaction Steps

6.13 g (47.1 mmol) of ethyl acetoacetate, 6.79 g (47.1 mmol) of 2,2-dimethyl-1,3-dioxane-4,6-dione and 3.99 g (51.8 mmol) of ammonium acetate were initially charged in 50 ml of acetic acid, and 5.053 ml (47.1 mmol) of 3-methylbutyraldehyde were added. The mixture was then stirred at an oil bath temperature of 130° C. overnight. After removal of the volatile components on a rotary evaporator, the residue was taken up in 100 ml of ethyl acetate and 100 ml of water were added. The aqueous phase was extracted with ethyl acetate. The combined organic phases were then washed with aqueous 2M sodium carbonate solution and then with concentrated aqueous sodium chloride solution. After drying with magnesium sulfate, the solvent was removed on a rotary evaporator. The crude product was taken up in 25 ml of diisopropyl ether and dissolved in the hot solvent. Crystallisation was then initiated with 3 ml of n-pentane. The precipitated solid was isolated by filtration and then washed with 2 ml of diisopropyl ether. Drying under high vacuum gave 1.40 g (12% of theory) of the target compound.

Provenance & Evidence