Dimethylacetamide → 1-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)ethanone

Participants

Reaction Steps

The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazole (50 mg, 0.134 mmol) and N,N-dimethylacetamide following General Procedure K. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (14 mg, 24%): 1H NMR (CDCl3, 600 MHz) δ 7.69 (s, 1H), 7.27-7.25 (m, 2H), 7.17-7.15 (m, 3H), 4.83 (t, 1H, J=7.0 Hz), 2.58 (t, 2H, J=7.5 Hz), 2.48 (s, 3H), 1.91-1.84 (m, 2H), 1.61-1.57 (m, 2H), 1.43-1.32 (m, 6H), 0.87 (s, 9H), 0.07 (s, 3H), −0.02 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 186.7, 169.5, 150.5, 143.6, 134.2, 129.2, 129.1, 126.5, 69.5, 37.2, 36.8, 32.2, 30.0, 30.0, 27.6, 26.5, 25.8, 19.1, −4.2, −4.3.

Provenance & Evidence