| Identification | Back Directory | [Name]
Methyl 4-oxotetrahydrofuran-3-carboxylate | [CAS]
57595-23-0 | [Synonyms]
Methyl 4-oxotetrahydrofur...
methyl 4-oxooxolane-3-carboxylate
Methyl 4-oxotetrahydrofuran-3-carboxylate
4-oxo-3-oxolanecarboxylic acid methyl ester
Tetrahydro-4-oxo-3-furoic acid methyl ester
Tetrahydro-4-oxo-3-furancarboxylic Acid Methyl Ester
3-Furancarboxylic acid, tetrahydro-4-oxo-, methyl ester | [Molecular Formula]
C6H8O4 | [MDL Number]
MFCD19707049 | [MOL File]
57595-23-0.mol | [Molecular Weight]
144.13 |
| Chemical Properties | Back Directory | [Boiling point ]
220℃ | [density ]
1.265 | [Fp ]
91℃ | [storage temp. ]
Inert atmosphere,2-8°C | [pka]
10.72±0.20(Predicted) | [Appearance]
Colorless to light pink Liquid | [InChI]
InChI=1S/C6H8O4/c1-9-6(8)4-2-10-3-5(4)7/h4H,2-3H2,1H3 | [InChIKey]
FCUDJBUBWCJOLK-UHFFFAOYSA-N | [SMILES]
O1CC(=O)C(C(OC)=O)C1 |
| Hazard Information | Back Directory | [Uses]
Tetrahydro-4-oxo-3-furancarboxylic Acid Methyl Ester, is used for the preparation of fused-pyrimidine derivatives as a series of novel GPR119 agonists. | [Synthesis]
Methyl ethanoate (4.5 g, 50 mmol) was added slowly and dropwise to a stirred slurry of anhydrous ether (40 mL) of sodium hydride (2.2 g, 55 mmol) at room temperature (rt). The reaction mixture was stirred continuously for 14 h at room temperature and then concentrated under vacuum. Subsequently, a solution of methyl acrylate (5.2 g, 55 mmol) in DMSO (20 mL) was added to the resulting solid at 0 °C and the mixture was stirred for 15 minutes. After removing the cooling bath, stirring was continued for 45 min. The reaction mixture was poured into 5% H2SO4 (60 mL) and extracted with ether (150 mL). The organic layer was dried, concentrated, and purified by column chromatography to yield methyl 4-oxotetrahydrofuran-3-carboxylate 1.7 g (24% yield).1H NMR (CDCl3) data were as follows: δ 4.51-4.40 (m, 2H), 4.03 (q, J = 8.1 Hz, 2H), 3.80 (s, 3H), 3.54 (t, J = 8.1 Hz 1H). | [References]
[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 5, p. 2124 - 2130
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 1124 - 1130
[3] Patent: WO2008/21456, 2008, A2. Location in patent: Page/Page column 32
[4] Patent: WO2018/137573, 2018, A1. Location in patent: Page/Page column 104
[5] Tetrahedron Letters, 1989, vol. 30, # 45, p. 6129 - 6132 |
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