Tetrahydrofuran → 3,4-dimethoxy-N-pent-4-enyl-N-phenyl-benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,4-dimethoxybenzanilide 33 (1.28 g, 5 mmol) and anhydrous cesium carbonate (4 equiv) in a mixture of anhydrous THF (14 mL) and DMF (56 mL) was added 5-bromo-pent-1-ene (2.85 g, 4 equiv) at room temperature and the mixture was heated at 80° C. for 72 h. The mixture was cooled, taken up in EtOAc and washed twice with water then brine. The organic layer was dried over magnesium sulfate, filtered and concentrated to dryness. The residue was purified by column chromatography on SiO2 (gradient of diethyl ether in petroleum ether) to afford the title compound 37 as a yellow oil (Yield 1.0 g, 62%).

Provenance & Evidence