Sodium hydride → 1-(4-Tert-butyldimethylsilyloxy-3-propylphenylmethyl)-3-carboethoxy-2-benzimidazolinone

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Reaction Steps

To a solution of 0.295 g (1.43 mmol) of 1-carboethoxy-2-benzimidazolinone dissolved in 5.0 mL DMF was added 0.063 g (1.57 mmol) of a 60% oil dispersion of sodium hydride and the resulting mixture was stirred under a nitrogen atmosphere and gently warmed with a heat gun until the solids had dissolved and gas evolution had ceased. A solution of the product of step A in 2.0 mL DMF was then added and the reaction mixture was stirred for an additional 0.5 hours. The mixture was then quenched with 10% aqueous citric acid and extracted into ethyl acetate. The organic layer was separated, washed with saturated sodium bicarbonate and brine, dried (MgSO4), filtered and evaporated, and then the residue was purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 0.088 g (64%) of the title compound.

Provenance & Evidence