Triethylamine → 1-Pyridine-4-yl-2-m-tolyl-ethane-1,2-dione

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Reaction Steps

Dimethylsufoxide (2.85 mL, 40 mmole) was dropwise added into a solution of trifluoroacetic anhydride (4.24 mL, 30 mmole) in methylene chloride (100 mL) at 78° C. The reaction mixture was stirred at that temperature for 10 min before the addition of 1-pyridine-4-yl-2-m-tolyl-ethane-1,2-diol (2.29 g, 10 mmole) in methylene chloride (50 mL). The mixture was stirred additional 1 hr at that temperature. Finally, the mixture was quenched with triethylamine (8.5 mL, 60 mmole) and the resulting mixture was allowed to warmed to r.t. The reaction was diluted with methylene chloride, washed with NH4Cl and brine, dried with MgSO4, evaporated, and finally, purified through a silica column (ethyl acetate/hexane) to give the title compound. MS (m/z): Calcd. C14H11NO2(M+): 225, found (M+H)+: 226.1.

Provenance & Evidence