Chemical Properties
CLEAR COLOURLESS LIQUID
Uses
Diethyl dimethylmalonate forms adducts with α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5-dimethanol based titanium catalysts
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General Description
Diethyl dimethylmalonate forms adducts with α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5-dimethanol based titanium catalysts.
Synthesis
1) Synthesis of diethyl 2,2-dimethylmalonate (Compound 1-2): Dissolve sodium (36 g, 1.56 mol) in 800 mL of anhydrous ethanol and cool in an ice water bath. Slowly add diethyl malonate (compound 1-1) (100 g, 0.62 mol) dropwise. After completion of the dropwise addition, continue the slow dropwise addition of iodomethane (97.3 mL, 1.56 mol). After completion of the dropwise addition, the ice water bath was removed and the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, 1000 mL of water was added to the mixture and extracted three times with 1000 mL of ethyl acetate. The organic phases were combined, washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated to give the crude product Compound 1-2 as a light yellow oil (102.1 g, 87.5% yield), which could be used in the next reaction without further purification.
References
[1] Molecules, 2016, vol. 21, # 5,
[2] Patent: US2014/179638, 2014, A1. Location in patent: Page/Page column
[3] Synthesis, 1985, # 1, p. 54 - 55
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 3, p. 365 - 368
[5] Patent: WO2015/95227, 2015, A2. Location in patent: Page/Page column 101
