Sodium hydride → HCID 118098781, compound

Participants

Reaction Steps

To a suspension of sodium hydride (0.019 g, 0.795 mmol) in DMSO (2 mL), was added trimethylsulfoxonium iodide (0.191 g, 0.867 mmol). The mixture was stirred at rt for 2 h. To the resultant clear solution was added to a solution of 36F (0.280 g, 0.723 mmol) in DMSO (2 mL) to give a yellow solution. The mixture was stirred at rt for 1 h, then at 60° C. for 5 h. Reaction mixture was quenched with sat. NH4Cl (10 mL), extracted with EtOAc (4×25 mL). Combined organic phase was washed with water (2×25 mL), brine (1×25 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified by flash chromatography (0-40% EtOAc/hexanes) to give 36G (0.144 g, 0.359 mmol, 49.6% yield) as a colorless syrup. MS (ESI) m/z: 402.2 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.33-7.58 (1H, m), 7.23 (1H, d, J=8.28 Hz), 6.91-7.11 (1H, m), 6.60-6.79 (1H, m), 4.71 (2H, br. s.), 2.82-2.98 (3H, m), 1.66 (2H, br. s.), 1.37-1.58 (18H, m), 1.19-1.32 (2H, m).

Provenance & Evidence