Ethyl 3-cyclopropyl-3-oxopropanoate

To ethyl acetate (100 ml) suspension of potassium ethyl malonate (17.0 g, 0.10 mol) were added triethylamine (34.7 ml, 0.25 mol) and magnesium chloride (14.3 g, 0.15 mol) with cooling with ice, and then the resulting mixture was stirred at 40°C for 20 hours. To tetrahydrofuran (50 ml) solution of cyclopropanecarboxylicacid (4.30 g, 50.0 mmol) were added oxalyl chloride (4.36 ml, 50.0 mmol) and a catalytic amount of N, N-dimethylformamide with cooling with ice, and the resulting mixture was stirred as such for 1 hour and then at room temperature for 1 hour. The above-mentioned malonic acid solution was added to this acid chloride solution with cooling with ice, and the resulting mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into 300 ml of aqueous 10 percent citric acid solution, and the mixture was extracted with ethyl acetate (300 ml .x. 3). The organic layer was successively washed with 500 ml of aqueous saturated sodium bicarbonate solution and 300 ml of brine, and dried over sodium sulfate. The solvent was evaporated, and7.26g (93percent) of the entitled compound was obtained as a colorless oil (this was directly used in the next reaction).1H-NMR(400MHz, CDCl3)δ: 0.94-0.99(2H, m), 1.10-1.15(2H, m), 1.28(3H, t, J=7.08Hz), 2.01-2.06(1H, m), 3.57 (2H, s), 4.21(2H, q, J=7.08Hz).To a solution of ethyl potassium malonate (6.5 g, 38.26 mmol) in acetonitrile was added MgClA. A. 48g of sodium tert-butoxide was added to 500mL of toluene, cooled to 10°C and 225g of dimethyl carbonate was added dropwise. After stirring for 30 min, 75.7g cyclopropyl methyl ketone was added dropwise and the reaction temperature was controlled not higher than 15°C. Stirring was continued for 30 min, and the reaction temperature was raised to 75°C overnight. The reaction was cooled to room temperature, the solution was poured into 500mL of ice water, adjusted pH1-2 with hydrochloric acid. The organic phase was washed with water and saturated sodium chloride solution, dried and concentrated to give 83g og an orange oil (A-3-2), yield: 60percent, purity: 98.28percent.a

Molecular Weight:156.18
XLogP3:0.7
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:156.078644241
Monoisotopic Mass:156.078644241
Topological Polar Surface Area:43.4
Heavy Atom Count:11
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes