[1071-46-1], C5H8O4, F.W. 132.12, b.p. 106°/3mm, f.p. >110°(230°F), d. 1.119, n20/D 1.4295, EINECS 213-992-7, BRN 1758845, MDL MFCD00020490, TSCA No
Hazard Codes: H315-H319-H335
Precautionary Codes: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501c
Reaction with alkyl chloroformates results in decarboxylation of the mixed anhydride in situ, providing a route to mixed ethyl alkyl malonates in high yield under very mild conditions: Tetrahedron Lett., 26, 1573 (1985).
Half esters of malonic acid react with ɑß-enals in pyridine/ DMAP to give ɑß δ-dienoic esters with good (E)-selectivity: Synthesis: 534 (1988).
The O,ɑ-dilithio-derivative, formed with n-BuLi in THF, can be acylated with acid chlorides to give, on acidic work-up (in situ decarboxylation), ß-ketoesters directly in high yield: J. Org. Chem., 44, 310 (1979); Org. Synth. Coll., 7, 213 (1990). Similarly, alkylation of the dilithio-derivative provides a direct route to esters of substituted acetic acids: J. Org. Chem., 40, 2556 (1975).
Carbodiimide coupling with polymer-bound ɑ-amino acids has been used in the solid-phase synthesis of substituted tetramic acids; J. Org. Chem., 63, 4808 (1998).
See also Ethyl potassium malonate, A10720 .
Fattorusso, C.; Persico, M.; Basilico, N.; Taramelli, D.; Fattorusso, E.; Scala, F.; Taglialatela-Scafati, O. Antimalarials based on the dioxane scaffold of plakortin. A concise synthesis and SAR studies. Bioorg. Med. Chem. 2011, 19 (1), 312-320.
Anwar, M.; Moloney, M. G. Chiral Bicyclic Tetramates as Non-Planar Templates for Chemical Library Synthesis. Chem. Biol. Drug Des. 2013, 81 (5), 645-649.