ChemicalBook CAS DataBase List 3-(4-CYANO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER

3-(4-CYANO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER synthesis

9synthesis methods

Product Name:3-(4-CYANO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER
CAS Number:49744-93-6
Molecular formula:C12H11NO3
Molecular Weight:217.22

619-65-8
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37517-78-5 Synthesis

37517-78-5
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3-(4-CYANO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER

49744-93-6
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$28.00/100mg

Yield:49744-93-6 34%

Reaction Conditions:

Stage #1:4-cyanobenzoic Acid with 1,1'-carbonyldiimidazole in tetrahydrofuran at 20;
Stage #2:magnesium bis(3-ethoxy-3-oxopropanoate) in tetrahydrofuran;acetonitrile at 20;Reflux;

Steps:

72
Intermediate 72 Ethyl 3-(4-cyanophenyl)-3-oxopropanoate A solution of 4-cyanobenzoic acid (5 g, 0.03 mol) and 1,1'-carbonyldiimidazole (6.6 g, 0.04 mol) in THF (80 ml) was stirred overnight at room temperature. Then a solution of the magnesium salt of malonic acid monoethyl ester (prepared via the dropwise addition of Et₃N (8.6 g, 0.085 mol) and MgCl₂ (10.5 g, 0.11 mol) to a solution of potassium 3-ethoxy-3-oxopropanoate (11 g, 0.065 mol) in acetonitrile (80 mL) was added to the reaction mixture, followed by stirring at room temperature for 2 h at 0° C. The reaction mixture was stirred overnight at reflux, quenched by the addition of water (300 mL), adjusted to pH 7 with HCl (3N), extracted with ethyl acetate (3*100 mL), and the organic layers were combined and dried over anhydrous magnesium sulfate and concentrated in vacuo to provide a residue, which was purified by silica gel column chromatography with 5% ethyl acetate in petroleum ether to afford ethyl 3-(4-cyanophenyl)-3-oxopropanoate as an orange solid (2.5 g, 34%). LC/MS (ES, m/z): [M+H]⁺ 218.0 ¹H-NMR (300 MHz, CDCl₃) δ 12.57 (s, 1H), 7.88-7.90 (m, 2H), 7.72-7.75 (m, 2H), 5.74 (s, 1H), 4.27-4.35 (m, 2H), 1.33-1.39 (m, 3H)

References:

BIOENERGENIX US2012/277224, 2012, A1 Location in patent:Page/Page column 57

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1443-80-7 Synthesis