Electric Literature of 10203-58-4,Some common heterocyclic compound, 10203-58-4, name is Diethyl isobutylmalonate, molecular formula is C11H20O4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To a solution of diethyl isobutylmalonate (50.0 g, 231 mmol) in anhydrous DMF (200 mL) cooled in an ice bath was added aH (60 %, 1 1.1 g, 277 mmol) in small portions. After the addition, the reaction mixture was stirred at 0C for 10 min and then at room temperature for 30 min. 5-Chloro-2-nirrobenzotrifluoride (47.3 g, 210 mmol) in anhydrous DMF (50 mL) was added dropwise and the mixture was stirred at room temperature for two days. The DMF was removed under high vacuum and the residue was diluted with ethyl acetate (400 mL). Water (400 mL) was added dropwise; ammonium chloride (25 g) was added and the layers were separated. The organic layer was washed with brine (400 mL), dried over sodium sulfate, and concentrated under reduced pressure to give a red-brown oil, which was purified by silica-gel flashchromatography eluting with heptane / ethyl acetate (12: 1) to give the desired product diethyl 2-isobutyl-2-(4-nilro-3-(trifiuoromethyl)phenyl)malonate (74.4 g, 87%) as a yellow oil:]H NMR (300 MHz, CDC13): delta 8.07 (s, 1 H), 7.94 (d, 2 H, J ——- 8.7 Hz), 7.88 (d, 2 I S . ./ 8.7 Hz), 4.25 (m, 4 H), 2.33 (d, 2 H, J= 6.6 Hz), 1.51 (m, 1 H), 1.26 (t, 6 H, J = 7.2 Hz), 0.84 (d, 6 H, J = 6.6 Hz);J 3C MR (75 MHz, CDC13): delta 169.23, 146.71 , 142.86, 132.94, 127.94 (q, J —— 5 Hz), 124.55, 123.12 (q, J —— 33 Hz), 121 .79 (q, J = 272Hz), 62.19, 65.59, 44.16, 24.66, 23.66, 13.89.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl isobutylmalonate, its application will become more common.
Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; KOENIG, Gerhard; BLAIN, Jean-francois; WO2013/106328; (2013); A1;,
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