Methyl 5-bromothiophene-2-carboxylate → Methyl 5-(2-(7-phenylheptanoyl)oxazol-5-yl)thiophene-2-carboxylate

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Reaction Steps

Methyl 5-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)thiophene-2-carboxylate. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (89 mg, 0.134 mmol) and methyl 5-bromothiophene-2-carboxylate following General Procedure A. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (65 mg, 94%): 1H NMR (CDCl3, 400 MHz) δ 7.72 (d, 1H, J=3.6 Hz), 7.26-7.23 (m, 4H), 7.17-7.14 (m, 3H), 4.80 (t, 1H, J=6.0 Hz), 3.89 (s, 3H), 2.58 (t, 2H, J=7.6 Hz), 1.95-1.87 (m, 2H), 1.68-1.56 (m, 2H), 1.38-1.27 (m, 6H), 0.88 (s, 9H), 0.09 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 167.4, 150.8, 147.9, 141.3, 139.2, 137.7, 133.5, 133.3, 130.7, 129.2, 129.2, 128.5, 73.7, 57.5, 41.4, 41.0, 36.5, 34.2, 30.8, 30.9, 30.2, 23.3, 0.2, 0.0.

Provenance & Evidence