3-Methylbutanal → HCID 59487372, compound

Participants

Reaction Steps

2.00 g (23.2 mmol) of ethyl-4,4,4-trifluoro-3-oxobutanoate, 3.35 g (23.2 mmol) of 2,2-dimethyl-1,3-dioxane-4,6-dione and 1.97 g (25.5 mmol) of ammonium acetate were initially charged in 20 ml of acetic acid, and 2.49 ml (23.2 mmol) of 3-methylbutyraldehyde were added. The mixture was then stirred at reflux temperature overnight. After removal of the volatile components on a rotary evaporator, another 8.95 g (116.1 mmol) of ammonium acetate were added to the residue, and the mixture was stirred at 180° C. overnight. After cooling, the mixture was taken up in 200 ml of ethyl acetate/water (1/1), and the aqueous phase was extracted with ethyl acetate (2×). The combined organic phases were dried with magnesium sulfate and the solvent was removed on a rotary evaporator. Work-up was carried out by column chromatography (silica gel: cyclohexane/ethyl acetate=4/1). Drying under high vacuum gave 1.40 g (19% of theory) of the target compound.

Provenance & Evidence