Propanedioic acid, ethylidene-, diethyl ester → HCID 136160528, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetamidine (2.47 g) and diethyl ethylidenemalonate (3.64 ml) were dissolved in ethanol (50 ml) and the mixture was stirred at 90° C. overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in water. The mixture was adjusted to pH 4 with 1 M hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and the obtained oil (570 mg) was dissolved in carbon tetrachloride (45 ml). N-Bromosuccinimide (381 mg), 2,2′-azobis(2-methylpropionitrile) (16 mg) and potassium carbonate (2.90 g) were added and the mixture was heated under reflux for 30 min. The reaction mixture was cooled to room temperature, and water was added. The aqueous layer was separated, adjusted to pH 3 with 1 M hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the object compound (313 mg) as a powder.

Provenance & Evidence