Dimethylformamide → 6-(2-Pyridyl)-methyloxy-2-acetylnaphthalene

Participants

Reaction Steps

To a solution of 6-hydroxy-2-acetylnaphthalene (1.04 g) in DMF (20 ml) were added sodium hydride (60%, 0.65 g) and 2-picolyl chloride hydrochloride (1.28 g) under ice-cooling and the resultant-mixture was stirred at room temperature for 12 hours. The reaction mixture was partitioned between toluene and water. The organic layer was washed with a saturated saline solution and dried over anhydrous magnesium sulfate. After concentration in vacuo, the residue was subjected to column chromatography on silica gel eluting with ethyl acetate/hexane to obtain the title compound (1.17 g, yield =75.5%). The NMR spectrum is as follows.

Provenance & Evidence