Sodium hydride → 2-(2-Morpholinoethoxy)benzaldehyde

Participants

Reaction Steps

To dried dimethylformamide (20 ml) solution in which 4-(2-hydroxyethyl)morpholine (1 g, 7.62 mmol) was dissolved, sodium hydride (201.2 mg, 8.38 mmol) was slowly added under nitrogen at room temperature. The mixture was stirred for 30 minutes at room temperature, and 4-fluorobenzaldehyde (1.1 g, 8.86 mmol) in dried dimethylformamide (5 ml) was added over 10 minutes. The reaction mixture was stirred at room temperature for 18 hours until the initial reaction product disappeared. Subsequently, 20 ml of ice water was added to the resulting mixture, and the mixture was extracted with ethyl acetate and water. The organic layer was washed with water several times, dried over anhydrous magnesium sulfate, filtered and solvent-evaporated. The residual oil was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to afford the intermediate compound 4-(2-(morpholinoethoxy)benzaldehyde (1.42 g, 79%).

Provenance & Evidence