Dimethylformamide → 6-Methoxy-2-naphthaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of butyllithium (50.6 ml of a 2.5M solution in hexanes, 126.5 mmol) in THF (200 mL) at -78° C., was added 2-bromo-6-methoxynaphthalene (15.00 g, 63.3 mmol) portionwise. Upon completion of addition, the mixture was stirred for 30 min at -78° C. N,N-Dimethylformamide (6.94 g, 94.95 mmol) was added dropwise. The cooling bath was withdrawn and the reaction allowed to warm to ambient temperature. It was then quenched with saturated aqueous NH4Cl (200 mL) and the THF was stripped off in vacuo. The aqueous residue was extracted with ethyl acetate (3×200 mL). The organics were combined, dried over MgSO4 and concentrated. The resulting residue was chromatographed (silica gel; 1:4 ether, hexanes) to afford 8.86 g (75%) of 6-methoxy-2-naphthalenecarboxaldehyde as a pale yellow solid.

Provenance & Evidence