ChemicalBook--->CAS DataBase List--->5751-81-5

5751-81-5

5751-81-5 Structure

5751-81-5 Structure
IdentificationBack Directory
[Name]

2-Thiophenecarboxylic acid, 5-Methyl-, ethyl ester
[CAS]

5751-81-5
[Synonyms]

Ethyl 5-methylthiophene-2-carboxylate
2-Thiophenecarboxylic acid, 5-Methyl-, ethyl ester
[Molecular Formula]

C8H10O2S
[MOL File]

5751-81-5.mol
[Molecular Weight]

170.23
Chemical PropertiesBack Directory
[storage temp. ]

Keep in dark place,Sealed in dry,Room Temperature
Hazard InformationBack Directory
[Uses]

Ethyl 5-methylthiophene-2-carboxylate is a useful reactant for the preparation of dithienylmaleimides via Perkin condensation, aminolysis and Suzuki coupling.
[Synthesis]

5-Methyl-2-thiophenecarboxylic acid

1918-79-2

Iodoethane

75-03-6

2-Thiophenecarboxylic acid, 5-Methyl-, ethyl ester

5751-81-5

To a solution of commercially available 5-methylthiophene-2-carboxylic acid (1.0 g, 7.04 mmol) and potassium carbonate (1.94 g, 14.08 mmol) in N,N-dimethylformamide (10 mL) was added ethyl iodide (1.65 g, 10.56 mmol) dropwise. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated to give ethyl 5-methylthiophene-2-carboxylate (400 mg, 34% yield) as a light yellow oil. Electrospray ionization mass spectrometry (ESI-MS) showed m/z 171 [M + H]+, which is consistent with the calculated value C8H10O2S. The intermediate can be used directly in the subsequent reaction without further purification or characterization.

[References]

[1] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 506 - 524
[2] Patent: WO2014/131855, 2014, A1. Location in patent: Page/Page column 63; 64
[3] Patent: WO2016/20307, 2016, A1. Location in patent: Page/Page column 45
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