3-(3,4-DIMETHOXY-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER synthesis
- Product Name:3-(3,4-DIMETHOXY-PHENYL)-3-OXO-PROPIONIC ACID METHYL ESTER
- CAS Number:74053-93-3
- Molecular formula:C12H14O5
- Molecular Weight:238.24
Yield:74053-93-3 98%
Reaction Conditions:
with sodium hydride in toluene; for 4 h;Inert atmosphere;Reflux;
Steps:
General Procedure A for the Preparation of Aryl-β-ketoesters (1a-h)
General procedure: To a dried three-necked flask equipped with a dropping funnel, a condenser, and a magnetic stirrer, dimethyl carbonate 5 (2 eq), NaH 60% (2.8 eq) and dry toluene (2 M) were added. The mixture was heated to reflux under nitrogen. A solution of the corresponding aryl-methyl-ketone (4a-h) (1 eq) in dry toluene (2 M) was added dropwise over 1 h. The resulting reaction mixture was refluxed for 3 h, and then was cooled to 0 °C and glacial acetic acid was added dropwise until pH 4. The solid obtained was filtered and subsequently dissolved in hot water. The aqueous phase was extracted with EtOAc(×3). The combined organic layers were washed with brine, dried over sodium sulphate, and concentrated in vacuo to give the desired Aryl β-Keto ester, which was pure enough to be used for the next step without purification.
References:
Galli, Ubaldina;Ciraolo, Elisa;Massarotti, Alberto;Margaria, Jean Piero;Sorba, Giovanni;Hirsch, Emilio;Tron, Gian Cesare [Molecules,2015,vol. 20,# 9,p. 17275 - 17287] Location in patent:supporting information
93-07-2
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