Methyl iodide → 2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-methyloxazole

Participants

Reaction Conditions

Reaction Steps

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazole (166 mg, 0.444 mmol) was dissolved in anhydrous THF (4 mL), cooled to −78° C. and t-BuLi (1.7 M in pentane, 1.3 equiv) was added dropwise under Ar. The reaction mixture was stirred for 2 h at −40° C., cooled to −78° C. and methyl iodide (3 equiv) was added dropwise and stirred for 1 h. The reaction mixture was warmed to room temperature, diluted with EtOAc, washed with saturated aqueous NaCl and dried over Na2SO4. Evaporation in vacuo yielded the crude product, which was purified by flash chromatography (0-2% EtOAc/hexanes) to afford the title compound as a clear oil (76 mg, 44%): 1H NMR (CDCl3, 600 MHz) δ 7.28-7.25 (m, 2H), 7.17-7.16 (m, 3H), 6.64 (s, 1H), 4.72 (t, 1H, J=7.2 Hz), 2.59 (t, 2H, J=7.8 Hz), 2.29 (s, 3H), 1.90-1.82 (m, 2H), 1.62-1.59 (m, 2H), 1.43-1.34 (m, 6H), 0.88 (s, 9H), 0.08 (s, 3H), −0.04 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 164.9, 143.7, 139.3, 129.2, 129.1, 126.4, 123.2, 69.5, 37.2, 36.8, 32.3, 30.0, 26.6, 26.6, 26.0, 19.1, 11.7, −4.2, −4.3.

Provenance & Evidence