Cesium carbonate → 1-(4-Hydroxyphenoxy)-2-(3-Methoxyphenyl)-6-Methoxynaphthalene

Participants

Reaction Steps

A solution of 1.5 g (4 mmol) of 1-(4-hydroxyphenoxy)-2-(3-methoxyphenyl)-6-methoxynaphthalene in 40 mL of DMF was prepared. To this solution was added 920 mg (5 mmol) of 2-chloroethylpiperidine hydrochloride and 5.2 g (16 mmol) of Cs2CO3, the reaction was stirred at ambient temperature under a nitrogen atmosphere for sixteen hours. The solvents were removed by evaporation and the residue partioned between water and EtOAc. The EtOAc layer was washed with water, then brine, dried with Na2SO4, and evaporated to dryness. The residue was dissolved in 10 mL of MeOH and 1 mL of 5N HCl was added. The solvents were removed by evaporation and the product crystallized from EtOAc. This yielded 1.8 g of the title compound as a white solid, mp 161-162° C.

Provenance & Evidence