2-(Dimethylamino)ethanol → 3-[2-(Dimethylamino)ethoxy]-4-methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(dimethylamino)ethanol (5.0 g, 56.0 mmol) and triethylamine (8.5 g, 84.0 mmol) in anhydrous DCM (50 mL) was added methanesulfonyl chloride (7.1 g, 62.0 mmol) at 0° C. under N2. The mixture was stirred at 0° C. for 1 hour. The solvent was removed in vacuo (6.0 g, yield 65%), and the crude was taken up in CH3CN (100 mL). 3-hydroxy-4-methoxybenzaldehyde (5.5 g, 36.0 mmol) and potassium carbonate (13.8 g, 100.0 mol) was added and reaction was refluxed under N2 overnight. An aqueous/EtOAc workup was followed, and crude was purified by silica gel column chromatography (PE:EtOAc=3:1) to give product (2.5 g, yield 31%) as yellow solid.

Provenance & Evidence