4-Bromoanisole → HCID 16110705, compound

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Reaction Steps

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-methoxyphenyl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (67 mg, 0.101 mmol) and 1-bromo-4-methoxybenzene following General Procedure B. Flash chromatography (5% EtOAc/hexanes) yielded the title compound as a clear oil (41 mg, 84%): 1H NMR (CDCl3, 500 MHz) δ 7.66 (d, 2H, J=9.0 Hz), 7.37-7.34 (m, 3H), 7.27-7.23 (m, 3H), 7.03 (d, 2H, J=9.0 Hz), 4.91 (t, 1H, J=5.5 Hz), 3.93 (s, 3H), 2.68 (t, 2H, J=7.5 Hz), 2.06-1.96 (m, 2H), 1.71-1.68 (m, 2H), 1.46-1.42 (m, 6H), 0.98 (s, 9H), 0.19 (s, 3H), 0.08 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 164.6, 160.2, 151.6, 143.2, 128.8, 128.7, 126.1, 126.0, 121.3, 120.3, 114.8, 69.1, 55.8, 36.8, 36.3, 31.9, 29.6, 26.2, 26.2, 25.6, 18.7, −4.5, −4.7.

Provenance & Evidence