Synthetic Route of 37746-78-4,Some common heterocyclic compound, 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, molecular formula is C6H9BrO2, 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.
A 6 N NaOH (0.1 mL) solution was added dropwise into a solution of 13 (100 mg, 0.38 mmol) and 30% H2O2 (0.05 mL) in EtOH (5 mL) at 0 C. The reaction mixture which resulted, was stirred for 2 h at the same temperature after which water was added to the reaction mixture and it was extracted with CH2Cl2 (2 * 10 mL). The combined organic extracts were washed with brine (2 * 15 mL). The organic layer was dried (MgSO4) and concentrated under vacuum to yield the crude epoxide ethyl ester. The crude compound was purified by flash column chromatography (10% EtOAc in hexanes) on silica gel to afford epoxide ethyl ester 29 (55 mg, 52%). 1H NMR (300 MHz, CDCl3): delta 7.99 (d, J = 8.4 Hz, 2H), 7.55 (d, J = 8.4 Hz, 2H), 4.46 (d, J = 1.8 Hz, 1H), 4.32 (m, 2H), 3.70 (d, J = 1.8 Hz, 1H), 1.38 (m, 12H); 13C NMR (75 MHz, CDCl3): delta 191.3, 167.31, 158.5, 132.5, 128.6, 126.0, 62.3, 55.2, 53.0, 35.3, 31.0, 14.1. HRMS (ESI) (M+Na)+, calcd for C16H20O4Na 299.1259; found 299.1248.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (E)-Ethyl 4-bromobut-2-enoate, its application will become more common.
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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