Reaction Steps
2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)benzamide. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (52 mg, 0.083 mmol) and 2-bromobenzamide following General Procedure A. Flash chromatography (20-40% EtOAc/hexanes) yielded the title compound as a white solid (39 mg, 100%): 1H NMR (CDCl3, 600 MHz) δ 7.70 (d, 1H, J=7.8 Hz), 7.60 (s, 1H), 7.51-7.48 (m, 2H), 7.39-7.36 (m, 1H), 7.25-7.23 (m, 2H), 7.16-7.13 (m, 3H), 6.48 (br s, 1H), 6.19 (br s, 1H), 4.88 (t, 1H, J=6.0 Hz), 2.57 (t, 2H, J=7.5 Hz), 1.93-1.87 (m, 2H), 1.59-1.56 (m, 2H), 1.44-1.30 (m, 6H), 0.87 (s, 9H), 0.09 (s, 3H), −0.02 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 170.4, 143.6, 137.6, 134.4, 132.5, 131.3, 130.7, 129.7, 129.2, 129.1, 128.6, 128.5, 126.4, 120.1, 69.3, 37.3, 36.8, 32.2, 30.0, 26.6, 26.6, 25.9, 19.0, −4.0, −4.3.
