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Dimethyl malonate is a reagent used in organic synthesis. It acts as a precursor for the synthesis of mono-substituted and di-substituted acetic acid, barbiturates, vitamin B1 and vitamin B6. It is used in the pharmaceutical industry to prepare pharmaceuticals like chloroquine and butazolidin. It is involved in the synthesis of diastereomeric pure thienylpyridines by reacting with 1,3-diphenylprop-2-enyl acetate.
For successive C-alkylation, using NaOMe/MeOH, followed by NaH/THF, see: Org. Synth. Coll., 8, 381 (1993). For Michael addition to ɑß-unsaturated acids, catalyzed by the Li salt of L-proline, see: J. Chem. Soc., Chem. Commun., 1088 (1991). For Knoevenagel reaction with (R)-citronellal, catalyzed by piperidine/AcOH, to give the alkylidene derivative, see: Org. Synth. Coll., 9, 310 (1998).
C-Arylation with ortho-nitroaryl halides can be accomplished with NaH in DMSO. The products can be readily converted to substituted oxindoles: Synthesis, 51 (1993):
Arylation with benzene: Tetrahedron Lett., 27, 2763 (1986), and free-radical substitution with thiophene or furan at the 2-position: Heterocycles, 27, 2627 (1988), are promoted by Ce(IV) salts.
See also Diethyl malonate, A15468.
Zhang, J.; Shao, Y.; Wang, Y.; Li, H.; Xu, D.; Wan, X. Transition-metal-free decarboxylation of dimethyl malonate: an efficient construction of α-amino acid esters using TBAI/TBHP. Org. Biomol. Chem. 2015, 13 (13), 3982-3987.
Mao, J.; Liu, D.; Li, Y.; Zhao, J.; Rong, G.; Yan, H.; Zhang, G. Temperature-controlled NaI-mediated α-oxybenzoylation or oxyacylation-decarboxylation reactions of dimethyl malonate with carboxylic acids. Catal. Commun. 2015, 70, 62-65.
Hazard Statements: H227
Precautionary Statements: P210u-P280a-P370+P378a-P403+P235-P501a
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