Reaction Steps
2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(6-methylpyridin-2-yl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (70 mg, 0.106 mmol) and 2-bromo-6-methylpyridine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a white solid (26 mg, 57%): 1H NMR (CDCl3, 400 MHz) δ 7.64 (s, 1H), 7.64 (t, 1H, J=7.6 Hz), 7.47 (d, 1H, J=7.6 Hz), 7.30-7.26 (m, 2H), 7.19-7.16 (m, 3H), 7.08 (d, 1H, J=7.6 Hz), 4.85 (dd, 1H, J=7.3, 5.8 Hz), 2.60 (t, 2H, J=7.6 Hz), 2.59 (s, 3H), 1.93 (m, 2H), 1.65 (m, 2H), 1.36 (m, 4H), 0.90 (s, 9H), 0.10 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 165.4, 158.8, 150.9, 146.8, 142.8, 137.0, 128.4, 128.2, 125.5, 124.8, 122.5, 116.1, 68.7, 36.4, 35.9, 31.4, 29.1, 25.7, 25.7, 25.1, 24.5, 13.6, −5.0, −5.2.
