Water → Allyl (2Z)-3-amino-4-(4-fluorophenyl)-2-butenoate

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Reaction Steps

Allyl 4-(4-fluorophenyl)-3-oxobutanoate (47 g, 198.95 mmol) and ammonium acetate (46.00 g, 596.85 mmol) were refluxed in benzene (250 mL) for 2 h with azeotropic removal of H2O and then cooled and concentrated. The residue was redissolved in Et2O and the organics washed with 1N HCl (2×), H2O, brine, and then dried (Na2SO4), filtered and concentrated to give 47 g (100% yield) of the title compound as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 7.17 (dd, J=8.4, 5.2 Hz, 2H), 6.99 (t, J=8.6 Hz, 2H), 5.28 (dd, J=17.2, 1.6 Hz, 1H), 5.18 (dd, J=10.3, 1.0 Hz, 1H), 4.61 (s, 1H), 4.55 (d, J=5.6 Hz, 2H), 3.41 (s, 2H).

Provenance & Evidence