These common heterocyclic compound, 4891-38-7, name is Methyl Phenylpropiolate, 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. Application In Synthesis of Methyl Phenylpropiolate
EXAMPLE 24 [3,5-diphenylisoxazole-4-yl]methyl carboxylate The benzonitrile oxide (0.98 mmoles) just prepared is added to the methyl 3-phenylpropiolate (157 mg, 0.98 mmoles) in anhydrous methylene chloride (5 ml) kept stirring at ambient temperature in an atmosphere of N2. The reaction mixture is kept stirring for 12 h, then blocked by adding H2O, The phases are separated and the aqueous phase is extracted with methylene chloride. The organic phases are combined, dried with anhydrous Na2SO4 and the solvent is distilled in a vacuum. Chromatography is performed on silica gel (eluent:petroleum ether/ethyl acetate=10:1). 184 mg of product are obtained (67% yield). M.p. 102.5-104.8 C. FT-IR (KBr): 3062, 2958, 1729, 1610, 1593, 1573, 1494, 1448, 1408, 1320, 1237, 1188, 1120, 1076, 1043, 941, 806, 768, 726, 697 cm-1. 1H NMR (300 MHz, CDCl3, delta): 7.96-7.88 (m, 2H, aromatic protons); 7.70-7.63 (m, 2H, aromatic protons); 7.56-7.46 (m, 6H, aromatic protons); 3.72 (s, 3H, CH3). 13C NMR (75 MHz, CDCl3, delta): 172.7, 163.2, 163.1, 131.6, 130.2, 129.1, 128.9, 128.8, 128.7, 128.6, 127.1, 102, 52.2. GC-MS (70 eV) m/z (rel.int.): 279 (M+, 79), 278 (17), 251 (6), 220 (5), 202 (7), 143 (10), 105 (100), 77 (47), 51 (9). Anal. Calc: for C17H13NO3: C, 73.11; H, 4.69; N, 5.02. Found: C, 73.06; H, 4.67; N, 5.06.
The synthetic route of Methyl Phenylpropiolate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Scilimati, Antonio; Vitale, Paola; Di Nunno, Leonardo; Patrignani, Paola; Tacconelli, Stefania; Capone, Marta Luciana; US2009/181970; (2009); A1;,
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