Réaction #320946

Équation de réaction

6-hydroxy-2-acetylnaphthalene

sodium hydride

2-picolyl chloride hydrochloride

DMF

→

title compound

Rendement 75.5%

6-(2-pyridyl)-methyloxy-2-acetylnaphthalene

Rendement 75.5%

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   AutreThe reaction mixture was partitioned between toluene and water
3. 3
   LavageThe organic layer was washed with a saturated saline solution
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   ConcentrationAfter concentration in vacuo

Mode opératoire

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.

Source