p-Toluenesulfonic acid → {2-Chloro-4-[(2-{[2-(2-hydroxyethoxy)ethoxy]methyl}phenyl)amino]phenyl}(2-methylphenyl)methanone

Participants

Reaction Steps

Compound 149 (5.68 g, 10.8 mmol) was dissolved in MeOH (100 mL) and p-toluenesulfonic acid (3.09 g, 16.3 mmol) was added. The solution was stirred at room temperature for 2 h. Aqueous NaHCO3 (5%, 100 mL) was added and the water phase was extracted with EtOAc (3×50 mL). The combined organic phases were washed with brine (50 mL), dried (MgSO4) and evaporated in vacuo. The crude product was purified by flash chromatography using EtOAc/Petroleum ether 1:1–3:2 as the eluent to afford the title compound as an orange oil.

Provenance & Evidence