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BenchChem - Model B011409 -Ethyl 4-(5-chloro-2-methoxyphenyl)-4-oxobutanoate
Ethyl 4-(5-chloro-2-methoxyphenyl)-4-oxobutanoate (ECB) is an organic compound that has been studied for its potential applications in scientific research. ECB is a colorless, odorless liquid that is soluble in water and ethanol. It is a derivative of the ethyl ester of 4-oxobutanoic acid and is used in a variety of laboratory experiments.
Chemical Reactions and Syntheses
Ethyl 4-(5-chloro-2-methoxyphenyl)-4-oxobutanoate is involved in various chemical reactions and syntheses. For example, it reacts with diethyl malonate in the presence of sodium hydride to produce diethyl 5-ethoxycarbonyl-3-oxohexanedioate and diethyl 5-carboxy-3-oxohexanedioate. Similar reactions with methyl cyanoacetate yield 1-ethyl methyl 5-cyano-3-oxohexanedioate and 1-ethyl hydrogen 5-cyano-3-oxohexanedioate (Kato, Kimura, & Tanji, 1978). Additionally, it can be used in a boric acid-catalyzed multi-component reaction in aqueous medium to synthesize 4H-isoxazol-5-ones efficiently (Kiyani & Ghorbani, 2015).
Biocatalysis and Enzymatic Reactions
Ethyl 4-(5-chloro-2-methoxyphenyl)-4-oxobutanoate is also a key substrate in biocatalysis and enzymatic reactions. Studies show its use in enzyme-catalyzed asymmetric reduction in organic solvent-water diphasic systems (Shimizu et al., 1990). Additionally, its reduction to ethyl (S)-4-chloro-3-hydroxybutanoate using Escherichia coli co-expressing carbonyl reductase and glucose dehydrogenase has been documented, highlighting its potential in biotechnological applications (Ye et al., 2010).
Organic Synthesis and Catalysis
In the field of organic synthesis, this compound is used for Knoevenagel condensations in ionic liquids, providing greener protocols for the production of various diastereomeric products (Paula et al., 2012). It also serves as a precursor for the synthesis of enantiopure intermediates for chiral drugs, as described in a review covering the biosynthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate ester (Ye, Ouyang, & Ying, 2011).
- IUPAC Name : ethyl 4-(5-chloro-2-methoxyphenyl)-4-oxobutanoate
- InChI : InChI=1S/C13H15ClO4/c1-3-18-13(16)7-5-11(15)10-8-9(14)4-6-12(10)17-2/h4,6,8H,3,5,7H2,1-2H3
- InChI Key : BDQAVOKECPGSNU-UHFFFAOYSA-N
- Canonical SMILES : CCOC(=O)CCC(=O)C1=C(C=CC(=C1)Cl)OC
- Molecular Formula : C13H15ClO4
- DSSTOX Substance ID : DTXSID70645846
- Molecular Weight : 270.71 g/mol
- Product Name : Ethyl 4-(5-chloro-2-methoxyphenyl)-4-oxobutanoate
- CAS RN : 107774-17-4
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