N-methoxy-N-methyl-2-phenylbenzo[d]oxazole-6-carboxamide → 1-(2-Phenyl-benzoxazol-6-yl)butan-1-one

Participants

Reaction Steps

To a solution of N-methoxy-N-methyl-2-phenylbenzo[d]oxazole-6-carboxamide (1.57 g, 5.6 mmol) in THF (20 mL) was added n-PrMgCl (2.0M in ether, 4.2 mL, 8.4 mmol, 1.5 eq) at 0° C. The mixture was warmed up to room temperature then stirred for 1 h. The reaction was quenched with saturated aqueous NH4Cl then extracted with EtOAc (3×40 mL). Solvent was removed then crude product was purified by flash column chromatography (0-20% EtOAc in hexanes) to afford the title compound (1.07 g, 4.0 mmol, 72%).

Provenance & Evidence