(Diethylamino)sulfur trifluoride → HCID 59305343, compound

Participants

Reaction Steps

3-[3-(4-Difluoromethoxy-phenylethynyl)-phenyl]-cyclobutanol (0.820 gm, 2.61 mmol) was dissolved in dichloromethane (10 ml) and treated with (diethylamino)sulfur trifluoride (DAST, 0.500 gm, 3.20 mmol). Upon completion of reaction as determined by thin layer chromatography (TLC) the crude material was absorbed onto silica and purified by column chromatography (gradient elution; 0%-10% EtOAc in hexanes) to yield an oil 267 mg (32%); 1H NMR (500 MHz, DMSO-d6) δ ppm 2.55-2.75 (m, 2H) 4.97-5.20 (m, 2H) 5.52-5.83 (m, 2H) 7.04-7.32 (m, 3H) 7.40-7.48 (m, 2H) 7.50-7.55 (m, 2H) 7.62 (d, J=8.8 Hz, 2H); MS (EI) m/z 316 [M+·].

Provenance & Evidence