N-Fluorobenzenesulfonimide → HCID 68524225, compound

Participants

Reaction Conditions

Reaction Steps

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazole (135 mg, 0.361 mmol) was dissolved in anhydrous THF (5 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., and N-fluorobenzenesulfonimide (1.5 equiv) was added in one portion. 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 aryl fluoride, which was purified by flash chromatography (0-2% EtOAc/hexanes) to afford the title compound as a clear oil (31 mg, 22%): 1H NMR (CDCl3, 500 MHz) 7.37-7.34 (m, 2H), 7.27-7.24 (m, 3H), 6.36 (d, 1H, J=9.0 Hz), 4.71 (t, 1H, J=7.2 Hz), 2.68 (t, 2H, J=7.8 Hz), 1.94-1.86 (m, 2H), 1.71-1.66 (m, 2H), 1.51-1.43 (m, 6H), 0.96 (s, 9H), 0.16 (s, 3H), 0.07 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 158.6 (d, J=292 Hz), 143.2, 128.8, 128.7, 126.0, 99.1 (d, J=12.8 Hz), 69.2, 36.4, 36.3, 31.8, 29.5, 29.5, 26.1, 25.4, 18.6, −4.7, −4.8.

Provenance & Evidence