ChemicalBook CAS DataBase List ETHYL (2-METHOXYBENZOYL)ACETATE

ETHYL (2-METHOXYBENZOYL)ACETATE synthesis

13synthesis methods

Product Name:ETHYL (2-METHOXYBENZOYL)ACETATE
CAS Number:41607-95-8
Molecular formula:C12H14O4
Molecular Weight:222.24

579-74-8 Synthesis

579-74-8
251 suppliers
$6.00/1g

105-58-8
484 suppliers
$14.00/25g

41607-95-8
78 suppliers
$27.00/100mg

Yield: 88%

Reaction Conditions:

Stage #1:2-Methoxyacetophenone with sodium hydride in tetrahydrofuran at 0 - 20; for 0.5 h;Inert atmosphere;
Stage #2:Diethyl carbonate in tetrahydrofuran at 20; for 14 h;Inert atmosphere;

Steps:

6 4.5.5 Ethyl 3-(2-methoxyphenyl)-3-oxopropanoate (2c)
Sodium hydride (480mg, 20.0 mmmol) was taken in dry THF (18mL) in a 100mL round bottom flask under N₂ and cooled it down to 0°C. To it was added a solution of ethyl 3-(2-methoxyphenyl)-3-oxopropanoate (1.0g, 6.7mmol) in THF (2mL). The reaction mixture was stirred at rt for 30min followed by the addition of diethyl carbonate (3.2mL, 26.8mmol). The reaction mixture was then stirred at rt for 14h. Ice-cooled water was added dropwise to quench the reaction. It was extracted with EtOAc (3×75mL). The combined organic layer was dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. The crude was further purified by flash chromatography on silica gel (60-120 mesh) using 10% hexane-EtOAc as eluent to afford 2c as a colourless liquid (1.3g, 88%). LC-MS (ESI) m/z 223.32 [M+H⁺]; 97% (purity).

References:

Zuniga, Edison S.;Korkegian, Aaron;Mullen, Steven;Hembre, Erik J.;Ornstein, Paul L.;Cortez, Guillermo;Biswas, Kallolmay;Kumar, Naresh;Cramer, Jeffrey;Masquelin, Thierry;Hipskind, Philip A.;Odingo, Joshua;Parish, Tanya [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 15,p. 3922 - 3946]

141-78-6 Synthesis