Abstract
Regioselective C- or O-alkylation of alkyl 4-hydroxy-2-methylthiophene-3-carboxylates with α-halo ketones is possible, depending on the solvent nature. A convenient preparative method of C-alkylation was proposed and previously not easily accessible β-hydroxythiophene derivatives were synthesized.
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S. Gronowitz and A.-B. Hörnfeldt, in The Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives, Ed. S. Gronowitz, Wiley, New York, 1986, Vol. 44, Part 2, Ch. 1.
B. Capon and F. C. Kwok, J. Am. Chem. Soc., 1989, 111, 5346.
J. Scramstad, A. Lunde, H. Hope, V. Bjørnstad, and P. Frøyen, J. Chem. Soc., Perkin Trans. 2, 2000, 1453.
G. A. Hurter and H. McNab, J. Chem. Soc., Chem. Commun., 1990, 375.
Y. Zhang, A.-B. Hörnfeldt, and S. Gronowitz, J. Heterocycl. Chem., 1993, 30, 129.
G. A. Hunter, Diss. Abstr. Int. B, 1992, 52, 5827; Chem. Abstr., 1993, 118, 124340k.
R. Lantz and A.-B. Hörnfeldt, Chem. Scripta, 1976, 10, 126.
A. Merz and C. Rem, J. Prakt. Chem. (Chem-Ztg.), 1996, 338, 672.
(a) E. B. Pedersen and S.-O. Lawesson, Tetrahedron, 1971, 27, 3861; (b) E. B. Pedersen and S.-O. Lawesson, Tetrahedron, 1972, 28, 2479.
(a) B. Cederlund and A.-B. Hörnfeldt, Chem. Scripta, 1975, 8, 140; (b) B. Cederlund and A.-B. Hörnfeldt, Acta Chem. Scand., 1971, 25, 3546; (c) B. Cederlund and A.-B. Hörnfeldt, Acta Chem. Scand., 1971, 25, 3657; (d) B. Cederlund and A.-B. Hörnfeldt, Acta Chem. Scand., 1971, 25, 3324.
E. Benary and A. Baravian, Chem. Ber., 1915, 48, 593.
R. Justoni, Chim. Ind. (Italy), 1942, 24, 195; Chem. Abstr., 1944, 38, 3610.
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Krayushkin, M.M., Shirinian, V.Z., Nikalin, D.M. et al. Regioselective C-alkylation of alkyl 4-hydroxy-2-methylthiophene-3-carboxylates with α-halo ketones. Russian Chemical Bulletin 53, 631–634 (2004). https://doi.org/10.1023/B:RUCB.0000035648.41262.77
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DOI: https://doi.org/10.1023/B:RUCB.0000035648.41262.77