Phthalamide → 2-[2-(Tritylsulfanyl)benzyl]-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

To a solution of (2-tritylsulfanylphenyl)-methanol (4.7 g, 12.3 mmol), phthalamide (2.29 g, 15.6 mmol) and thiphenylphosphine (4.09 g, 15.6 mmol) in THF (70 mL) at 0° C. under an argon atmosphere, was slowly added DEAD (2.4 mL, 15 mmol). The reaction mixture was stirred at RT for 30 min, then partitioned between aqueous saturated NaHCO3 and EtOAc. The organic layer was separated, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo to afford the title compound (4.7 g, 75%) as yellow foam. 1H NMR (300 MHz, CDCl3): δ 7.82 (2H, m), 7.70 (2H, m), 7.38-7.33 (5H, m), 7.27-7.22 (10H, m), 7.12 (1H, dd, J 1.4, 0.5), 7.08 (1H, dt, J 1.4, 0.5), 6.96 (1H, dd, J 7.6, 1.5), 6.88 (1H, dt, J 7.6, 1.5), 4.47 (2H, s).

Provenance & Evidence