Sodium hydride → Ammonium Hydroxide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-phenylimidazol-2-one (1.00 g, 6.24 mmol) in DMP (10 mL) at 0° C. was added sodium hydride (300 mg of a 60% dispersion in mineral oil, 7.49 mmol). The mixture was stirred at 0° C. for 1 h, then tert-butyl bromoacetate (1.47 g, 7.49 mmol) was added. The reaction mixture was allowed to warn to ambient temperature and stirring was continued for 18 h. The reaction mixture was poured into water and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give a crude product, which was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 90:5:0.5 to provide the title compound. MS: m/z=275 (M+1).

Provenance & Evidence