Reaction Steps
The reaction of hydroxylamine 82 (0.71 g, 2 mmol) with α,α,α-trifluoro-m-tolualdehyde (60) (0.348 g, 2 mmol) afforded, after workup, a light yellow solid. The crude product was recrystallized from ether/petroleum ether to obtain 0.80 g (1.55 mmol. 78%) of 85 as a white crystalline solid: mp 127°-129° C.; IR (CH2Cl2) 3440, 2980, 1698, 1624, 1558, 1475, 1332, 1300, 1215, 1100, 1018, 810 cm-1 ; 1H NMR (CDCl3) δ 1.14 (d, J=6.2 Hz, 3H), 1.26 (d, J=6.2 Hz, 3H), 2.29 (s, 6H), 3.65 (s, 3H), 4.97 (septet, J=6.2 Hz, 1H), 5.08 (s, 1H), 6.47 (br s, 1H), 7.28-8.76 (m, 9H); 13C NMR (CDCl3) δ 19.48, 21.99, 22.22, 39.98, 51.15, 67.31, 102.99, 103.70, 119.43, 121.55, 125.52, 125.55, 127.22, 128.56, 129.28, 130.43, 131.46, 131.92, 133.40, 144.79, 145.33, 148.92, 149.91, 167.01, 168.03. Anal. Calcd for C27H27N2O5F3 : C, 62.79; H, 5.23. Found: C, 62.68; H, 5.02.
