Methyl thiophene-2-carboxylate

clear light yellow liquid

Methyl thiophene-2-carboxylate serves as a synthetic equivalent of the pentanoate 5-anion for preparing long-chain esters[3]. Promoted by samarium diiodide, it undergoes three-component coupling with N-methylindole-2-carbaldehyde and 4-methoxyacetophenone, or reacts with acetophenones and aryl methyl ketones to afford diols[1][2]. It also couples with 4-chloroacetophenone and 4-methoxyacetophenone to yield diol products[2].

ChEBI: Methyl thiophene-2-carboxylate is a thiophenecarboxylic acid.

[1] Babu, G., Yu, H.-M., Yang, S.-M., & Fang, J.-M. (2004). Carbazolothiophene-2-carboxylic acid derivatives as endothelin receptor antagonists. Bioorganic & Medicinal Chemistry Letters, 14(5), 1129–1132. https://doi.org/10.1016/j.bmcl.2003.12.067
[2] Yang, S.-M., Shie, J.-J., Fang, J.-M., Nandy, S. K., Chang, H.-Y., Lu, S.-H., & Wang, G. (2002). Synthesis of Polysubstituted Benzothiophenes and Sulfur-Containing Polycyclic Aromatic Compounds via Samarium Diiodide Promoted Three-Component Coupling Reactions of Thiophene-2-carboxylate. The Journal of Organic Chemistry, 67(15), 5208–5215. https://doi.org/10.1021/jo0257849
[3] Yang, S.-M., Nandy, S. K., Selvakumar, A. R., & Fang, J.-M. (2000). Distant Functionalization via Incorporation of Thiophene Moieties in Electrophilic Reactions Promoted by Samarium Diiodide. Organic Letters, 2(23), 3719–3721. https://doi.org/10.1021/ol006628w