Hexamethylphosphoramide → HCID 11991896, compound

Participants

Reaction Conditions

Reaction Steps

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(trifluoromethyl)oxazole 2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-iodooxazole (24 mg, 0.048 mmol), HMPA (5 equiv), CuI (1.2 equiv) and FSO2CF2CO2CH3 (5 equiv) were dissolved in DMF (1 mL) and heated to 70° C. in a sealed vial for 5 h. The mixture was cooled to room temperature, saturated aqueous NH4Cl was added and the aqueous layer was extracted with ether. The ether layer was washed with saturated aqueous NaHCO3, washed with saturated aqueous NaCl and dried over sodium sulfate. Flash chromatography (0-2% EtOAc/hexanes) yielded the title compound as a light yellow oil (12 mg, 55%): 1H NMR (CDCl3, 600 MHz) δ 7.38 (s, 1H), 7.28-7.25 (m, 2H), 7.18-7.15 (m, 3H), 4.81 (t, 1H, J=6.0 Hz), 2.59 (t, 2H, J=7.8 Hz), 1.90-1.82 (m, 2H), 1.61-1.59 (m, 2H), 1.43-1.33 (m, 6H), 0.87 (s, 9H), 0.07 (s, 3H), −0.04 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 168.5, 143.6, 140.5 (d, J=45 Hz), 129.2, 129.1, 128.8 (d, J=2.7 Hz), 126.5, 119.7 (d, J=265 Hz), 69.3, 37.0, 36.8, 32.2, 29.9, 26.5, 26.5, 25.8, 19.0, −4.4, −4.4.

Provenance & Evidence