| Identification | Back Directory | [Name]
ETHYL TRIMETHYLACETOPYRUVATE | [CAS]
13395-36-3 | [Synonyms]
AKOS MSC-0258
-2,4-dioxohexanoate
Ethyl pivaloylpyruvate
ETHYL TRIMETHYLACETOPYRUVATE
1ETHYL TRIMETHYLACETOPYRUVATE
Ethyl trimethylacetopyruvate,98%
Ethyl trimethyacetopyruvate, 98+%
3-Pivaloylpyruvic acid ethyl ester
Ethyl-5,5-dimethyl-2,4-dioxohexanoat
Ethyl 2,4-dioxo-5,5-dimethylhexanoate
ETHYL 5,5-DIMETHYL-2,4-DIOXOHEXANOATE
trimethylacetopyruvic acid ethyl ester
Ethyl 5, 5-dimethyl2, 4-dioxo-1-hexanoate
2,4-Dioxo-5,5-dimethylhexanoic acid ethyl ester
5,5-Dimethyl-2,4-dioxo-hexanoic acid ethyl ester
(Z)-ethyl 2-hydroxy-5,5-diMethyl-4-oxohex-2-enoate
Hexanoic acid, 5,5-dimethyl-2,4-dioxo-, ethyl ester
Ethyl (trimethylacetyl)pyruvate, Ethyl 5,5-dimethyl-2,4-dioxocaproate
Ethyl 5,5-dimethyl-2,4-dioxohexanoate~Trimethylacetopyruvic acid ethyl ester | [EINECS(EC#)]
236-478-4 | [Molecular Formula]
C10H16O4 | [MDL Number]
MFCD00052319 | [MOL File]
13395-36-3.mol | [Molecular Weight]
200.23 |
| Chemical Properties | Back Directory | [Boiling point ]
64 °C | [density ]
1.046±0.06 g/cm3(Predicted) | [refractive index ]
1.4700 | [Fp ]
68-70°C/0.5mm | [storage temp. ]
2-8°C | [form ]
clear liquid | [pka]
6.98±0.46(Predicted) | [color ]
Light yellow to Brown | [BRN ]
510374 | [InChI]
InChI=1S/C10H16O4/c1-5-14-9(13)7(11)6-8(12)10(2,3)4/h5-6H2,1-4H3 | [InChIKey]
NIMKIMUBJFWPTD-UHFFFAOYSA-N | [SMILES]
C(OCC)(=O)C(=O)CC(=O)C(C)(C)C | [CAS DataBase Reference]
13395-36-3 |
| Hazard Information | Back Directory | [Synthesis]
A mixture of pinacolone (740 mmol) and diethyl oxalate (820 mmol) was added dropwise to a solution of sodium ethoxide (prepared by dissolving 740 mmol of sodium in 450 mL of ethanol) at room temperature, followed by stirring the reaction for 1 hour at 78 °C. Upon completion of the reaction, the reaction mixture was cooled to room temperature and slowly poured into a pre-cooled aqueous 5 M hydrochloric acid solution (800 mL). Extraction was carried out with methyl tert-butyl ether (300 mL each time, 3 times in total), and the combined organic phases were washed with saturated aqueous sodium chloride solution (500 mL) and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to afford the target product ethyl 5,5-dimethyl-2,4-dioxohexanoate as a red liquid. Product weight: 140 g, yield: 93.3%. Mass spectrum (ES+): m/z 199 ([M+H]+). Nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3): δ 6.5 (1H, s, CH), 4.3 (2H, q, OCH2), 1.35 (3H, t, CH3), 1.15 (9H, s, 3×CH3). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 18, p. 4383 - 4388
[2] Journal of Organic Chemistry, 1997, vol. 62, # 17, p. 5908 - 5919
[3] Patent: WO2009/71707, 2009, A1. Location in patent: Page/Page column 43
[4] Chinese Chemical Letters, 2016, vol. 27, # 4, p. 566 - 570
[5] Chinese Chemical Letters, 2016, vol. 27, # 2, p. 251 - 255 |
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