ChemicalBook CAS DataBase List 3-CYCLOPROPYL-3-OXO-PROPIONIC ACID ETHYL ESTER

3-CYCLOPROPYL-3-OXO-PROPIONIC ACID ETHYL ESTER synthesis

13synthesis methods

Product Name:3-CYCLOPROPYL-3-OXO-PROPIONIC ACID ETHYL ESTER
CAS Number:24922-02-9
Molecular formula:C8H12O3
Molecular Weight:156.18

6148-64-7 Synthesis

6148-64-7
383 suppliers
$5.00/10g

4023-34-1 Synthesis

4023-34-1
353 suppliers
$12.00/5g

3-CYCLOPROPYL-3-OXO-PROPIONIC ACID ETHYL ESTER

24922-02-9
204 suppliers
$5.00/1g

Yield:24922-02-9 93%

Reaction Conditions:

Stage #1:ethyl potassium malonate with triethylamine;magnesium chloride in ethyl acetate at 0 - 40; for 20 h;
Stage #2:cyclopropanecarboxylic acid chloride in tetrahydrofuran;ethyl acetate at 0 - 20; for 20 h;

Steps:

73 Reference Example 73; Ethyl 3-cyclopropyl-3-oxopropionate (I-73)
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 % citric acid solution, and the mixture was extracted with ethyl acetate (300 ml × 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 (93%) 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).

References:

DAIICHI PHARMACEUTICAL CO., LTD. EP1479681, 2004, A1 Location in patent:Page 59

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765-43-5 Synthesis