Reference of 37746-78-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 37746-78-4 as follows.
To a solution of ethyl 4-bromocrotonate 23 (0.9 mL, 5.18 mmol) in anhydrous dioxane (10 mL), palladium triphenyl phosphine tetrakis (300 mg, 0.26 mmol) was added to the round bottom flask. The flask was then evacuated three times at rt and backfilled with argon. The reaction mixture was allowed to stir for 15 min at rt then phenyl boronic acid (1.84 g, 10.36 mmol) and Na2CO3 (2.75 g, 25.9 mmol) were added under a positive pressure of argon. The reaction mixture which resulted was heated at reflux for 18 h and then cooled to rt. It was then passed through a short bed of celite. The celite bed was washed with EtOAc (50 mL) and the combined organic layers were washed with water (50 mL) and brine (30 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The crude oil was purified by flash column chromatography (5% EtOAc in hexanes) on silica gel to afford ester 18 (893 mg, 70%). 1H NMR (300 MHz, CDCl3): delta 7.37 (d, J = 8.1 Hz, 2H), 7.14 (d, J = 7.8 Hz, 2H), 7.12 (d, J = 15.6 Hz, 1H), 5.85 (d, J = 15.3 Hz, 1H), 4.21 (q, J = 7.2 Hz, 2H), 3.52 (d, J = 6.9 Hz, 2H), 1.35 (S, 9H), 1.31 (t, J = 6.9 Hz, 3H); 13C NMR (75 MHz, CDCl3): delta 166.5, 149.6, 147.5, 134.7, 128.5, 125.6, 122.2, 60.2, 38.0, 34.4, 31.4, 14.3. HRMS (ESI) (M+Na)+, calcd for C16H22O2Na 269.1518; found 269.1512.
According to the analysis of related databases, 37746-78-4, the application of this compound in the production field has become more and more popular.
Reference:
Article; Tiruveedhula, V.V.N. Phani Babu; Witzigmann, Christopher M.; Verma, Ranjit; Kabir, M. Shahjahan; Rott, Marc; Schwan, William R.; Medina-Bielski, Sara; Lane, Michelle; Close, William; Polanowski, Rebecca L.; Sherman, David; Monte, Aaron; Deschamps, Jeffrey R.; Cook, James M.; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7830 – 7840;,
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