Sodium hydride → HCID 118093092, compound

Participants

Reaction Steps

To a suspension of sodium hydride (60% suspension in mineral oil) (0.019 g, 0.473 mmol) in DMSO (2.5 mL), was added trimethylsulfoxonium iodide (0.284 g, 1.291 mmol). The mixture was stirred at rt for 2 h. To the solution was added 15E (0.187 g, 0.430 mmol) in DMSO (2.5 mL) to give a yellow solution. The mixture was stirred at rt for 1 h, quenched with sat. NH4Cl (10 mL), extracted with EtOAc (4×15 mL). Combined organic phase was washed with water (2×10 mL), brine (1×10 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified by flash chromatography (0-40% EtOAc/hexanes). Fractions were combined and concentrated under reduced pressure to give 15F (0.173 g, 90% yield) as a colorless syrup. MS (ESI) m/z: 449.1 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.34-7.50 (1H, m), 7.20 (1H, d, J=8.08 Hz), 6.83-6.96 (1H, m), 6.44 (1H, br. s.), 4.51 (2H, br. s.), 4.07 (2H, q, J=7.16 Hz), 2.82 (3H, br. s.), 1.35-1.72 (22H, m), 1.15 (3H, t, J=7.07 Hz).

Provenance & Evidence