2-Iodophenol → 1-(5-(2-Hydroxyphenyl)oxazol-2-yl)-7-phenylheptan-1-one

Participants

Reaction Steps

2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenol. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (88 mg, 0.134 mmol) and 2-iodophenol following General Procedure A. Flash chromatography (10-30% EtOAc/hexanes) yielded the title compound as a clear oil (21 mg, 34%): 1H NMR (CDCl3, 500 MHz) δ 7.80-7.76 (m, 1H), 7.62 (s, 1H), 7.56 (br s, 1H), 7.36-7.20 (m, 6H), 7.09-7.04 (m, 2H), 4.94 (t, 1H, J=6.0 Hz), 2.62 (t, 2H, J=7.5 Hz), 2.05-1.93 (m, 2H), 1.68-1.65 (m, 2H), 1.47-1.32 (m, 6H), 0.97 (s, 9H), 0.17 (s, 3H), 0.07 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 166.3, 154.3, 148.8, 143.2, 130.0, 128.8, 128.6, 126.5, 126.0, 124.9, 119.2, 116.8, 115.6, 70.1, 37.0, 35.3, 31.8, 29.6, 26.2, 26.2, 25.5, 18.6, −4.4, −4.6.

Provenance & Evidence