Dimethylformamide → 6-Methoxy-2-naphthaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-6-methoxynaphthalene (0.5 g, 2.11 mmol) in THF (10 mL) at -78° C., was added n-butyllithium (1.69 mL of a 2.5M in hexanes, 4.22 mmol) dropwise and the solution was stirred for 45 min at -78° C. N,N-dimethylformamide (0.31 g, 4.22 mmol) was then added and the reaction was allowed to stir for 15 min at -78° C. The reaction was quenched with saturated aqueous NH4Cl(10 mL). This solution was extracted with ethyl acetate (3×10 mL). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 15:85) afforded 345 mg (88%) of 6-methoxy-2-napthaldehyde as an off-white solid.

Provenance & Evidence