Reaction Steps
The reaction of hydroxylamine 55 (0.80 g, 2 mmol) with 5-nitro-2-furaldehyde (65) (0.282 g, 2 mmol) afforded, after workup, a purple oil. The crude product was purified by flash chromatography with 1:1 ethyl acetate/hexane as the eluant to obtain 0.85 g (1.61 mmol, 81%) of 76 as a brown gum; IR (CH2Cl2) 3440, 1698, 1622, 1528, 1470, 1350, 1215, 1100, 1012, 810 cm-1 ; 1H NMR (CDCl3) δ 1.09 (d, J=6.2 Hz, 3H), 1.23 (d, J=6.2 Hz, 3H), 2.33 (s, 6H), 3.35 (s, 3H), 3.55-3.59 (m, 2H), 4.17-4.21 (m, 2H), 4.94 (septet, J=6.2 Hz, 1H), 5.09 (s, 1H), 6.20 (s, 1H), 7.34-8.29 (m, 7H); 13C NMR (CDCl3) δ 19.49, 19.59, 21.92, 22.18, 40.22, 58.85, 62.91, 67.36, 70.73, 103.11, 103.88, 113.84, 116.76, 118.98, 120.73, 122.43, 128.83, 131.37, 144.54, 145.28, 147.09, 149.47, 150.02, 151.63, 166.83, 167.31. Anal. Calcd for C26H29N3O9 : C, 59.20; H, 5.50. Found: C, 59.47; H, 5.74.
