Reaction Steps
The reaction of hydroxylamine 55 (1.97 g, 5 mmol) with 2-chlorobenzaldehyde (61) (0.70 g, 5 mmol) afforded, after workup, a light yellow oil. The crude product was purified by flash chromatography with 3:5 ethyl acetate/petroleum ether as the eluant to obtain 2.11 g (4.0 mmol, 80%) of 72 as a light yellow gum: IR (CH2Cl2) 3440, 2940, 1690, 1623, 1590, 1550, 1470, 1295, 1202, 1100; 1H NMR (CDCl3) δ 1.10 (d, J=6.2 Hz, 3H), 1.22 (d, J=6.2 Hz, 3H), 2.25 (s, 6H), 3.30 (s, 3H), 3.54 (t, J=4.8 Hz, 2H), 4.16 (m, 2H), 4.93 (septet, J=6.2 Hz, 1H), 5.07 (s, 1H), 6.87 (s, 1H), 7.27-9.45 (m, 9H); 13C NMR (CDCl3) δ 19.69, 19.84, 22.49, 22.72, 40.43, 59.36, 63.40, 67.70, 71.18, 103.32, 104.11, 120.08, 122.09, 127.76, 128.94, 129.04, 129.76, 130.22, 130.94, 131.28, 132.16, 134.30, 145.57, 146.32, 149.83, 150.49, 167.51, 167.99. Anal. Calcd for C28H31N2O6Cl: C, 63.81; H, 5.88. Found: C, 63.51; H, 6.02.
