Sodium hydride → N-(6-(4-(benzyloxy)butoxy)-3-formylpyridin-2-yl)pivalamide

Participants

Reaction Steps

To a solution of 4-(benzyloxy)butan-1-ol (15.42 g, 85.6 mmol) in DMF (120 mL) was added sodium hydride (4.11 g, 171 mmol) at 0° C. The mixture was stirred for 20 min, then intermediate 6 (10.28 g, 42.7 mmol) was added portion-wise and the resulting mixture was stirred overnight. The mixture was quenched with saturated aq NH4Cl and extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel column (elution with PE/EtOAc=8:1-4:1) to give N-(6-(4-(benzyloxy)butoxy)-3-formylpyridin-2-yl)pivalamide (intermediate 7) (5.04 g, 31%).

Provenance & Evidence