N-Formylmorpholine → 8-methoxy-4H-benzo[1,3]dioxine-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To 500 ml of a THF solution containing 31.2 g of 6-bromo-8-methoxy-4H-benzo[1,3]dioxine there was added dropwise 55 ml of n-butyllithium (2.55 M, hexane solution) at −70° C. under a nitrogen atmosphere. After stirring for 30 minutes at −72° C., 20 ml of N-formylmorpholine was added and the temperature was raised from −78° C. to 0° C. over a period of 30 minutes. A saturated ammonium chloride aqueous solution was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered out and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane system) to obtain the target compound (21.28 g) as a colorless solid.

Provenance & Evidence