Ethyl 4-aminocinnamate → ethyl (2E)-3-{4-[(4-dec-1-ynylbenzyl)amino)phenyl}acrylate

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Reaction Steps

The title compound was prepared following the procedure A using 4-dec-1-ynyl-benzaldehyde and ethyl (2E)-3-(4-aminophenyl)acrylate. (purification by flash chromatography on SiO2, EtOAc/c-Hex 1/7 to 1/6 in about 30 min.) as a yellow solid (61%). 1H NMR (CDCl3) δ: 7.59 (d, J=15.8 Hz, 1H), 7.36 (m, 4H), 7.26 (m, 2H), 6.57 (d, J=8.7 Hz, 2H), 6.21 (d, J=15.8 Hz, 1H), 4.35 (s, 2H), 4.23 (dd, J1=7.2 Hz, J2=14.3 Hz, 2H), 2.39 (t, J=7.2 Hz, 2H), 1.66-1.52 (m, 2H), 1.50-1.39 (m, 2H), 1.38-1.24 (m, 11H), 0.87 (m, 3H). M+ (ESI): 418.1; M− (ESI): 416.2. HPLC, Rt: 6.1 min (purity: 98.7%).

Provenance & Evidence