Reaction Steps
2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-(trifluoromethyl)pyridin-2-yl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (130 mg, 0.196 mmol) and 2-chloro-4-(trifluoromethyl)pyridine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (80 mg, 77%): 1H NMR (CDCl3, 400 MHz) δ 8.79 (d, 1H, J=5.0 Hz), 7.84 (s, 1H), 7.73 (s, 1H), 7.43 (dd, 1H, J=5.0, 0.9 Hz), 7.28-7.24 (m, 2H), 7.18-7.15 (m, 3H), 4.88 (dd, 1H, J=7.3, 5.9 Hz), 2.60 (t, 2H, J=7.8 Hz), 1.93 (m, 2H), 1.61 (m, 2H), 1.36 (m, 4H), 0.91 (s, 9H), 0.11 (s, 3H), 0.01 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 166.5, 150.9, 149.6, 148.6, 142.8, 139.3 (q, J=33.9 Hz), 128.4, 128.2, 126.6, 125.6, 118.1 (q, J=3.5 Hz), 114.6 (q, J=3.0 Hz), 68.7, 36.4, 35.9, 31.4, 29.1, 25.7, 25.7, 18.2, −5.0, −5.1.
