Dichloromethane → 2-(2-{4-[1-(3-Bromo-phenyl)-vinyl]-phenoxy}-ethoxy)-tetrahydro-pyran

Participants

Reaction Conditions

Reaction Steps

Cesium carbonate (4.36 g, 13.4 mmol, 1.2 eq) and 2-(2-bromoethoxy)-tetrahydro-2H-pyran (1.94 mL, 12.8 mmol, 1.2 eq) were added to a solution of 4-[1-(3-bromo-phenyl)-vinyl]-phenol (2.9 g, 10.7 mmol, 1.0 eq) in dry N,N-dimethylformamide (35 mL). The mixture was stirred overnight at 55° C. Dichloromethane (100 mL) and water (50 mL) were then added. The organic phase was washed with water (3×) and dried over sodium sulfate. Evaporation of solvent and purification by flash chromatography (eluent: cyclohexane/ethyl acetate=9:1 then 8:2) gave 2.0 g of desired product as yellow oil (yield 47%).

Provenance & Evidence