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Helvetica Chimica Acta – Vol. 96 (2013)
5 arom. H); 5.03 (dd, J ¼ 6.8, 8.4, CH); 3.29 (d, J ¼ 6.8, 1 H of CH2); 3.27 (d, J ¼ 8.4, 1 H of CH2); 2.30 (s,
Me).
7. Mixed Anhydride of 9d and Subsequent Ammonolysis. To a soln. of 9d (3.392 g, 15 mmol) and
Et3N (2.2 ml, 1.52 g, 15 mmol) in dried CH2Cl2 (30 ml) was added ethyl carbonochloridate (1.5 ml, 1.63 g,
15 mmol), dropwise under stirring at 08. The resulting soln. was stirred for 30 min to generate the mixed
anhydride 10d, which was directly treated with 25% aq. NH3 soln. (4 ml). The mixture was stirred for 2 h.
The org. phase was separated, the aq. phase extracted with AcOEt (3 ꢁ 25 ml), the combined org. phase
washed with sat. NaCl soln. (3 ꢁ 25 ml) and dried (Na2SO4), the solvent evaporated, and the residue
subjected to CC: cinnamamide (¼(2E)-3-phenylprop-2-enamide (3d; 1.92 g, 87%). Colorless crystals.
M.p. 152 – 1538 ([28]: 148 – 1518). 1H-NMR (400 MHz): 7.65 (d, J ¼ 15.6, CH); 7.52 – 7.36 (m, 5 arom. H);
6.47 (d, J ¼ 15.6, COCH); 5.84 (br. s, NH2).
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