Water → HCID 131729983, compound

Participants

Reaction Steps

To a suspension of compound 73 (11.97 g) in CH3CN (125 mL) was added 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (75) (30 g) and CsF (20 g). The mixture was stirred at room temperature for 3 days. Water was added to quench the reaction and most of the CH3CN was removed via rotavaporator. The residue was extracted with EtOAc, washed with water and brine, and dried over MgSO4. After concentration of the solvent, the crude product was purified by silica gel chromatography, eluting with a gradient of 100% hexane to 80% EtOAc/hexane over 30 min. The pure product was isolated as a brown oil. 1H NMR (CDCl3) δ 7.30-7.24 (m 3H), 7.21-7.15 (m, 3H), 7.01 (dd, 1H, J=5.1, 9.6 Hz), 6.87 (d, 2H, J=8.7 Hz), 5.62 (d, 2H, J=9.6 Hz), 4.31 (d, 1H, J=5.1 Hz), 3.81 (s 3H), 1.65 (s, 3H).

Provenance & Evidence