Adding a certain compound to certain chemical reactions, such as: 3377-20-6, name is Diethyl 2-methylenemalonate, 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 3377-20-6, COA of Formula: C8H12O4
nBuLi solution (2.5 M in hexanes, 2.4 mL, 6.0 mmol) was added, dropwise over 4 min., to a cooled (-20 C bath maintained by an immersion cooler) solution of N,N,N?-trimethylethylenediamine (655 mg, 6.41 mmol) in 2-MeTHF (14 mL). After stirring for 15 min., 4-tert-butoxybenzaldehyde (1.02 g, 5.72 mmol) was added via syringe by mass difference dropwise over 5 min. After 15 min., more nBuLi solution (2.5 M in hexanes, 6.9 mL, 17 mmol) was added, dropwise over 4 min. After stirring at this temperature for 24 h, the reaction mixture was cooled in a dry ice/acetone bath. After stirring for 20 min., diethyl ketomalonate (3.6 mL, 23 mmol) was added to the reaction mixture, dropwise over 8 min. After 5 min., the reaction was quenched by rapid addition of aq. HCl (2.0 M, 12.5 mL), and cooling was ended. The resulting mixture was partitioned between dichloromethane and half-saturated brine. The aqueous layer was extracted once more with dichloromethane, and the combined organic layers were dried (sodium sulfate) and concentrated to a clear, yellow oil (5.45 g). Chromatographic purification (354 g silica gel, heptane to 3:7 EtOAc/heptane gradient) afforded the title compound as a white solid (1.06 g, 53 % yield, ca. 90 % purity). LCMS (ESI) m/z: 375.3[M+Na] (19 %). 1H NMR (400 MHz, CDCl3) delta 1.29 (t, J = 7.1 Hz, 3H), 1.33 (t, J = 7.1 Hz, 3H), 1.35 (s, 9H), 2.48 (d, J = 7.8 Hz, 1H), 4.24 (dq, J = 10.8, 7.1 Hz, 1H), 4.32 (dq, J = 10.8, 7.1 Hz, 1H), 4.34 (dq, J = 10.7, 7.1 Hz, 1H), 4.38 (dq, J = 10.8, 7.1 Hz, 1H), 5.85 (dt, J = 7.8, 0.6 Hz, 1H), 6.64 (dd, J = 8.1, 2.0 Hz, 1H), 6.66 (dt, J = 2.0, 0.5 Hz, 1H), 7.27 (dt, J = 8.2, 0.6 Hz, 1H). 13C NMR (101 MHz, CDCl3) delta 13.9 (1C), 14.1 (1C), 28.8 (3C), 62.7 (1C), 62.7 (1C), 76.1 (1C), 79.3 (1C), 93.6 (1C), 106.4 (1C), 118.2 (1C), 120.2 (1C), 125.3 (1C), 158.6 (1C), 159.3 (1C), 165.3 (1C), 166.4 (1C).
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Reference:
Article; Rocke, Benjamin N.; Conn, Edward L.; Eisenbeis, Shane A.; Ruggeri, Roger B.; Tetrahedron Letters; vol. 53; 41; (2012); p. 5467 – 5470;,
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