Uses
Methyl isobutyrylacetate is used for the synthesis if heterocycles (Furane, Pyrazolone, Chinilone) and building block for pharmaceuticals (reducer of cholesterol). Product Data Sheet
Synthesis
The general procedure for the synthesis of methyl isobutyrylacetate from 3-methyl-2-butanone and dimethyl carbonate was as follows: first, sodium hydride (70.32 g, 2.1 eq., 50% dispersion in oil) was washed with toluene, and the washings were decanted. Next, anhydrous toluene (500 mL) and dimethyl carbonate (329.3 g, 2 eq.) were added to the reaction system and the stirred mixture was heated to 80 °C under nitrogen protection. Meanwhile, 3-methyl-2-butanone (120 g, 1 eq.) was dissolved in 240 mL of toluene and slowly added to the reaction system. After the reaction lasted for 5 hours, the cooled mixture was poured into a mixture containing glacial acetic acid (300 mL) and water (120 mL). The organic layer was separated and the aqueous layer was further extracted with ethyl acetate (300 mL). All organic extracts were combined and after evaporation of the solvent, the residue was distilled to afford methyl 4-methyl-3-oxopentanoate as a slurry (138 g, 62.72% yield).
References
[1] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 4, p. 923 - 926
[2] Patent: WO2006/110918, 2006, A1. Location in patent: Page/Page column 51
[3] Organic and Biomolecular Chemistry, 2011, vol. 9, # 3, p. 739 - 743
[4] Chemistry - A European Journal, 2008, vol. 14, # 32, p. 9864 - 9867
[5] Advanced Synthesis and Catalysis, 2016, vol. 358, # 12, p. 1934 - 1941
