| Identification | More | [Name]
DIETHYL OXALPROPIONATE | [CAS]
759-65-9 | [Synonyms]
2-ETHOXALYLPROPIONIC ACID ETHYL ESTER
2-OXALPROPIONIC ACID DIETHYL ESTER
DIETHYL 2-METHYL-2'-OXOSUCCINATE
DIETHYL 2-METHYL-3-OXOSUCCINATE
DIETHYL 2-OXALPROPIONATE
DIETHYL METHYLOXALACETATE
DIETHYL OXALOPROPIONATE
DIETHYL OXALPROPIONATE
ETHYL 2-ETHOXALYLPROPIONATE
METHYLOXALACETIC ACID DIETHYL ESTER
methyloxo-butanedioicacidiethylester
diethyl 2-methyloxosuccinate
methyloxo-butanedioic acid diethyl ester
2-Methyl-3-oxobutanedioic acid diethyl ester
2-Methyl-3-oxosuccinic acid diethyl ester | [EINECS(EC#)]
227-750-3 | [Molecular Formula]
C9H14O5 | [MDL Number]
MFCD00009163 | [Molecular Weight]
202.2 | [MOL File]
759-65-9.mol |
| Chemical Properties | Back Directory | [Boiling point ]
138 °C/23 mmHg (lit.) | [density ]
1.073 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.432(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Hexane (Slightly), Methanol (Slightly) | [form ]
Oil | [pka]
9.30±0.46(Predicted) | [color ]
Clear Colourless to Pale Yellow | [BRN ]
1783697 | [InChI]
InChI=1S/C9H14O5/c1-4-13-8(11)6(3)7(10)9(12)14-5-2/h6H,4-5H2,1-3H3 | [InChIKey]
OQOCQBJWOCRPQY-UHFFFAOYSA-N | [SMILES]
C(OCC)(=O)C(C)C(=O)C(OCC)=O | [CAS DataBase Reference]
759-65-9(CAS DataBase Reference) | [EPA Substance Registry System]
Butanedioic acid, methyloxo-, diethyl ester (759-65-9) |
| Hazard Information | Back Directory | [Uses]
Diethyl Oxalopropionate is a useful precursor in the synthesis of 2-Methylcitric Acid (M265080); a metabolite of Citric Acid (C521000) that can also be formed from condensation of propionoyl-CoA and oxaloacetic acid catalyzed by a citrate synthase enzyme. | [Uses]
Reactant involved in:• ;Synthesis of anticancer and antiviral agents1• ;Oxidation by organohypervalent iodine reagent2• ;Synthesis of monomers for preparation of functional polyesters3• ;Synthesis of calpain inhibitors4• ;Preparation of human A2A receptor antagonists5• ;Structural studies of dihydropteroate synthase inhibitors6 | [Definition]
ChEBI: Diethyl 2-methyl-3-oxosuccinate is an alpha-ketoester, a beta-ketoester, an ethyl ester and a diester. | [Synthesis]
At room temperature, diethyl oxalate (300 g, 2.94 mol) and ethyl propionate (429.4 g, 2.94 mol) were dissolved in 1.8 L of anhydrous ethanol, followed by the addition of sodium ethoxide (300 g, 4.41 mol). The reaction mixture was stirred overnight. After completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted to 7 with 6 N hydrochloric acid. subsequently, the mixture was concentrated under reduced pressure to remove the solvent. The concentrated residue was diluted with water and extracted with ethyl acetate. The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give diethyl oxalylpropionate (400 g, 67% yield) as a red liquid, which could be used in subsequent steps without further purification.1H NMR (400 MHz, CDCl3) δ ppm: 4.103-4.386 (m, 5H); 1.246-1.439 (m, 9H) . | [References]
[1] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9701 - 9708
[2] Patent: US2015/25087, 2015, A1. Location in patent: Paragraph 0168; 0237; 0238
[3] Journal of the American Chemical Society, 1946, vol. 68, p. 132
[4] Justus Liebigs Annalen der Chemie, 1888, vol. 246, p. 329
[5] Journal of the Chemical Society, 1924, vol. 125, p. 313 |
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