Reaction Steps
3-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)benzonitrile. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (60 mg, 0.091 mmol) and 3-bromobenzonitrile following General Procedure A. Flash chromatography (2-5% EtOAc/hexanes) yielded the title compound as a clear oil (31 mg, 72%): 1H NMR (CDCl3, 600 MHz) δ 7.91 (s, 1H), 7.84 (d, 1H, J=7.8 Hz), 7.59 (d, 1H, J=7.8 Hz), 7.53 (t, 1H, J=7.8 Hz), 7.36 (s, 1H), 7.27-7.24 (m, 2H), 7.16-7.15 (m, 3H), 4.83 (t, 1H, J=6.0 Hz), 2.58 (t, 2H, J=7.8 Hz), 1.95-1.88 (m, 2H), 1.65-1.59 (m, 2H), 1.36-1.33 (m, 6H), 0.89 (s, 9H), 0.10 (s, 3H), −0.01 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 166.8, 149.8, 143.6, 132.3, 130.7, 130.2, 129.2, 129.1, 128.9, 128.3, 126.5, 124.2, 119.1, 114.2, 69.5, 37.3, 36.8, 32.3, 30.0, 26.6, 26.6, 26.0, 19.1, −4.1, −4.2.
