Methanol → HCID 59497689, compound

Participants

Reaction Steps

To a solution of 1-naphthalen-1-ylmethyl-1,3-dihydro-benzimidazol-2-one (200 mg, 0.73 mmol) in DMF (3.0 mL) are added methyl acrylate (0.07 mL, 0.8 mmol) and 40% benzyltrimethyl ammonium hydroxide in MeOH (0.03 mL, 0.073 mmol). The resulting mixture is stirred at room temperature for 1.5 h and then Sat. NH4Cl (5 mL) and water (20 mL) are added. The mixture is extracted with EtOAc (3×50 mL) and the organic layers are combined, washed with water (3×75 dried over MgSO4 and concentrated to give crude product. Purification by flash column chromatography using 30% EtOAc in Hexanes affords 220 mg (84%) of 3-(3-naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid methyl ester.

Provenance & Evidence