Reaction Steps
2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(2-fluorophenyl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (75 mg, 0.113 mmol) and 1-fluoro-2-iodobenzene following General Procedure A. Flash chromatography (2% EtOAc/hexanes) yielded the title compound as a clear oil (52 mg, 98%): 1H NMR (CDCl3, 400 MHz) 7.77 (dt, 1H, J=9.6, 5.6 Hz), 7.42 (d, 1H, J=4.0 Hz), 7.31-7.21 (m, 4H), 7.18-7.13 (m, 4H), 4.85 (t, 1H, J=6.0 Hz), 2.59 (t, 2H, J=7.2 Hz), 1.90-1.93 (m, 2H), 1.62-1.60 (m, 2H), 1.33-1.36 (m, 6H), 0.90 (s, 9H), 0.11 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 169.7, 163.4 (d, J=250 Hz), 150.6, 157.9, 134.4 (d, J=8.3 Hz), 133.5, 133.3, 131.2 (d, J=12.6 Hz), 131.1, 131.1, 130.7, 129.6 (d, J=3.2 Hz), 121.7 (d, J=13.0 Hz), 120.1 (d, J=20.9 Hz), 73.8, 41.6, 41.0, 36.5, 34.3, 34.3, 30.9, 30.3, 23.3, 0.2, 0.0.
