Potassium Carbonate → 6-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a 3-necked round bottom flask, add 1-chloro-6-methoxy-3,4-dihydronaphthalene-2-carbaldehyde (2.25 g, 10.1 mmol), 4-(2-(piperidin-1-yl)ethoxy)phenol (1.8 g, 8.24 mmol), tetra-N-butylammonium iodide (50 mg, 0.14 mmol), potassium carbonate (4.1 g, 29.8 mmol), and 4-dimethylaminopyridine (120 mg, 0.99 mmol). Purge the reaction vessel with nitrogen. Add dimethylformamide (30 mL) slowly to the reaction. Heat the mixture to 100° C. with stirring and hold for 4 hours. Cool the reaction mixture to room temperature and quench with ice-water. Extract the mixture with ethyl acetate three times. Dry the combined organic layers over MgSO4, filter, and concentrate to give 6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carbaldehyde (4.11 g).

Provenance & Evidence