Electric Literature of 10203-58-4, These common heterocyclic compound, 10203-58-4, name is Diethyl isobutylmalonate, its 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.
2-lsobuty3malonic acid diethyl ester (40. Og, 0.185 rnol) in DMF (50mL) was added dropwise to a stirred suspension of sodium hydride (60% in mineral oil, 8.0g, 0.33 mol) in 200 mL DMF (200mL) over 20 rain, at 0C under nitrogen. The mixture was stirred for 0.5 h at room temperature, cooled to 0 C and l,2,4-trifluoro-5-nitro-benzene (30. Og, 169.5 mmol) in DMF (150mL) was added dropwise. The resulting reaction mixture was stirred at room temperature for 16b, poured into ice water (2 OOmL) and extracted with EtOAc (3×1 OOmL). The combined organic phases were washed with water (3×1 OOmL), brine (lOOmL) and dried (MgS04).Evaporation of solvent under reduced pressure ga ve a brown oil which was purified by column chromatography over silica gel (Fle tane-EtOAc, gradient) to give 57.0 g (90%) of 2-(2,5- difluoro-4-nitropheny3)-2-isobuty3malonic acid diethyl ester as yellow oil.3FI NMR (300 MHz,CDCI3/TMS): delta 7.87 (dd, J = 12.3, 6.0 Flz, 1H), 7.79 (dd, J = 10.1 , 6.4 Hz, 1 H), 4.30-4.18 (m, 4H), 2.27 (d, J = 5.8 Hz, 2H), 1.60-1.50 (m, i l l ). 1.26 (t, J = 7.1 Hz, 6H), 0.82 (d, J = 7.0 Hz, 6H);3C NMR (75 MHz, CDClv’TMS): delta 168.2, 155.1 (d, Ja= 252.3 Hz), 150.9 (d, CF = 263.2 Hz), 135.7, 135. L 120.0 (dd,2JCF= 26.0,1= 4.0 Hz), 113.0 (d,2JC¥= 29.0 Hz), 62.3, 43.1 , 24.9, 23.8, 13.8.
Statistics shows that Diethyl isobutylmalonate is playing an increasingly important role. we look forward to future research findings about 10203-58-4.
Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; KOENIG, Gerhard; BLAIN, Jean-francois; WO2013/106328; (2013); A1;,
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