4-Fluoroiodobenzene → 1-(5-(4-Fluorophenyl)oxazol-2-yl)-7-phenylheptan-1-one

Participants

Reaction Steps

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-fluorophenyl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (81 mg, 0.122 mmol) and 1-fluoro-4-iodobenzene following General Procedure A. Flash chromatography (2% EtOAc/hexanes) yielded the title compound as a clear oil (40 mg, 61%): 1H NMR (CDCl3, 600 MHz) δ 7.63-7.61 (m, 2H), 7.27-7.24 (m, 4H), 7.17-7.11 (m, 4H), 4.88 (t, 1H, J=6.0 Hz), 2.58 (t, 2H, J=7.5 Hz), 1.95-1.90 (m, 2H), 1.62-1.59 (m, 2H), 1.46-1.35 (m, 6H), 0.89 (s, 9H), 0.10 (s, 3H), −0.01 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 165.9, 163.5 (d, J=258 Hz), 151.5, 143.6, 129.2, 129.1, 127.1 (d, J=8.3 Hz), 126.4, 124.8, 121.1, 117.0 (d, J=22 Hz), 69.4, 37.3, 36.8, 32.3, 30.0, 26.6, 26.6, 25.9, 19.1, −4.1, −4.2.

Provenance & Evidence