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Ethyl propiolate is used as a precursor in the preparation of substituted anthraquinones and pyrazolo[1,5-a]pyridine, which exhibits anti-inflammatory activity. Further, it is employed in the synthesis of benzene-1,2,3,5-tetracarboxylates promoted by triphenylphosphine. Its halogenated derivatives are used as a substrate for direct, asymmetric alkynylation of cyclic beta-ketoesters using chiral phase-transfer catalysts.
n-BuLi gives the alkynyllithium derivative, stable at low temperatures: J. Org. Chem., 45, 28 (1980). For use in a sequence for the synthesis of butenolides, see: J. Am. Chem. Soc., 101, 1544 (1979):
Conjugate addition of allylic alcohols in the presence of trimethylamine proceeds via an intermediate betaine and leads to allyl vinyl ethers which undergo the Claisen rearrangement to give δ-unsaturated aldehydes: J. Org. Chem., 48, 5406 (1983); Org. Synth. Coll., 8, 536 (1993):
Regio- and stereospecific hydrohalogenation of propiolic acid derivatives is illustrated by the conversion of ethyl propiolate to (Z)-3-bromo-2-propenoate in the presence of LiBr + acetic acid in acetonitrile: J. Org. Chem., 57, 709 (1992); Org. Synth. Coll., 9, 412 (1998).
Al-Masum, M.; Shaban, W. Microwave irradiated Pd-catalyzed C(sp)-H activation and cross-coupling with styryltrifluoroborates. Tetrahedron Lett. 2015, 56 (11), 1437-1440.
Iwata, A.; Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides. Tetrahedron 2015, 71 (37), 6580-6585.
Gefahrenhinweise (EU): H226-H315-H319-H335
Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
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