Ethyl Acetate → 3-(4-Bromophenyl)-1-methyl-4-[[2-(trimethylsilyl)ethoxy]methyl]-4,5-dihydro-1H-1,2,4-triazol-5-one

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Reaction Steps

To a solution of compound 51b (1.0 g, 3.9 mmol) in DMF (5 mL) was added sodium hydride (0.2 g, 5.0 mmol) in portions at 0° C. The mixture was stirred for 20 min, then 2-(trimethylsilyl)ethoxymethyl chloride (0.73 g, 4.4 mmol) was added dropwise. The reaction mixture was stirred at rt for 2 h. EtOAc (100 mL) was added. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated to give a residue, which was purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:5 v/v)) to afford compound 51c as a yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C15H22BrN3O2Si: 384.1 (M+H). Found 384.1.

Provenance & Evidence