Acetic Acid → 2-Cyano-3-propyl-hex-2-enoic acid benzyl ester

Participants

Reaction Steps

To a mixture of 4-heptanone (2.0 mL, 14.3 mmol) and benzyl cyanoacetate (2.51 g, 14.3 mmol) at 0° C. was added acetic acid (0.08 mL, 1.43 mmol), then piperidine (0.14 mL, 1.43 mmol) dropwise. The ice bath was removed, and stirring continued for 10 min. Additional acetic acid (0.08 mL) and piperidine (0.14 mL) were added, followed by the additional of oven-dried 4A molecular sieves such that stirring was not impeded. The mixture was stirred for 1 h, then partitioned between EtOAc and sat. sodium bicarbonate (NaHCO3) (aq). The phases were separated, and the organic phase washed with brine, dried (MgSO4), and concentrated to provide 1.03 g (27%) of 2-cyano-3-propyl-hex-2-enoic acid benzyl ester as a colorless oil. 1H NMR (CDCl3) δ 7.35 (m, 5H), 5.24 (s, 2H), 2.71 (m, 2H), 2.52 (m, 2H), 1.60 (m, 2H), 1.49 (m, 2H), 1.00 (t, J=7.3 Hz, 3H), 0.95 (t, J=7.3 Hz, 3H). 13C NMR δ 182.46, 161.72, 135.37, 128.83, 128.58, 128.21, 115.87, 104.77, 67.26, 40.77, 35.80, 22.36, 21.86, 14.54, 14.32. LRMS: m/z 272.1 (M+1). IR (neat) 2223, 1729 cm−1. Anal. Calcd for C17H21NO2: C, 75.25; H, 7.80; N, 5.16. Found: C, 75.44; H, 7.80; N, 5.22.

Provenance & Evidence