ORGANIC SPECTROSCOPY INTERNATIONAL: Ethyl (E)-3-(2-Acetamido-4-methylphenyl)acrylate

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Ethyl (E)-3-(2-Acetamido-4-methylphenyl)acrylate

mp = 155−156 °C; R_f = 0.06 (n-hexane/EtOAc 3:1);

¹H NMR pdf(400 MHz, CDCl₃) δ: 1.32 (t, J=7.1 Hz, 3 H), 2.22 (s, 3 H), 2.34 (s, 3 H), 4.24 (q, J=7.0, 2 H), 6.34 (d, J=15.9 Hz, 1 H), 7.00 (d, J=7.63 Hz, 1 H), 7.44 (d, J=7.8 Hz, 2 H), 7.54 (br s, 1 H), 7.77 (d, J=15.9 Hz, 1 H);

¹³C NMR pdf(100 MHz, CDCl₃) δ: 14.3, 21.3, 21.4, 23.7, 60.5, 118.6, 125.6, 126.5, 126.6, 127.0, 136.1, 139.1, 141.2, 167.1, 169.7; IR (neat): 3225, 1711, 1661, 1635, 1610, 1537, 1492, 1164, 983, 813 cm^-1; MS m/z [M]⁺: 247, 204, 160, 132, 117.

HRMS [M + H⁺] calcd for C₁₄H₁₈NO₃: 248.12812, found: 248.12787; [M + Na⁺] calcd for C₁₄H₁₇NNaO₃: 270.11006, found: 270.10978

The analysis is performed applying coupled gas chromatography/mass spectrometry instrument 7890A GC-System with mass detector5975C (Triplex-Axis-Detector) from Agilent Technologies equipped with HP-5MS column (30 m x 0.25 mm, film 0.25 μm). Retention time t_ret = 7.41 min with 3 mL·min^-1 of He, temperature profile T = 70 °C/1 min, then 70-150 °C/2.7 min, then 150 °C/1 min, then 150-250 °C/2.9 min, then 250 °C/3 min, then 250-290 °C/1 min.

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