Adding a certain compound to certain chemical reactions, such as: 685-88-1, name is Diethyl fluoromalonate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 685-88-1, Formula: C7H11FO4
General Procedure: In a small vial, MBH carbonate 1a-e (0.25 mmol, 1 equiv), 2-fluoromalonate 2, (67 mg, 0.375 mmol, 1.5 equiv), and catalyst I (8 mg, 0.025 mmol, 10 mol %) in 1 mL of toluene were stirred at room temperature overnight. The crude mixture was monitored by 1H NMR and after completion the crude was purified by column chromatography, affording compound 3. 1,1-diethyl 3-methyl 1-fluoro-2-phenylbut-3-ene-1,1,3-tricarboxylate (3a):1H NMR (400 MHz, CDCl3) delta 7.31-7.28(m, 2H), 7.24-7.20(m, 2H), 6.37-6.37(m, 1H), 6.17(m, 1H), 5.08 (d, JH-F = 35.2 Hz, 1H), 4.24-4.22 (m, 2H), 4.03-4.02(m, 2H), 3.63(s, 3H), 1.24-1.22(t, J = 7.1 Hz, 3H), 1.03-1.02(t, J = 7.1 Hz, 3H). 13C NMR (100 MHz, CDCl3) delta 166.2, 165.2, 164.9, 164.8, 164.5, 138.1, 138.1, 134.9, 129.8, 129.8, 128.2, 127.8, 127.02, 126.9, 98.0, 95.9, 62.9, 62.7, 52.2, 49.0, 48.8, 13.8, 13.7; 19F NMR (376 MHz, CDCl3) delta -174.1 (d, J = 35.4 Hz). HRMS (ESI) calcd. for C18H25FNO6 (M+NH4)+, 370.1666 found 370.1665. Enantiomeric excess: 81%, -65.6 (CHCl3; c = 0.8 g/100 mL) determined by HPLC (Daicel Chiralpak IA, i-PrOH/Hexane = 5/95), UV 254 nm, flow rate 0.8 mL/min, major 9.7 min, minor 10.9 min.
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Reference:
Article; Wang, Bing; Companyo, Xavier; Li, Jing; Moyano, Albert; Rios, Ramon; Tetrahedron Letters; vol. 53; 32; (2012); p. 4124 – 4129;,
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