Dimethylformamide → HCID 178500163, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of potassium carbonate (0.1783 g, 1.290 mmol), tetrabutylammonium hydrogen sulfate (0.005110 g, 0.01505 mmol) and N,N-dimethylformamide (3.00 mL, 38.7 mmol) was added 2-(4-tert-butyl-cyclohexyloxy)-6-(1-nitro-ethyl)-naphthalene (0.3821 g, 1.075 mmol). The mixture was stirred for 15 minutes, then methyl acrylate (0.1162 mL, 1.290 mmol) was added while maintaining the temperature at 20° C. (cool water bath). The mixture was stirred and allowed to reach room temperature. Stirring was continued (in slightly below room temperature water bath) for 2 hours and the reaction was monitored by HPLC. Ethylacetate and saturated aq. ammonium chloride were added and the layers were separated. The combined organic layer was dried over MgSO4, filtered, concentrated and purified by flash chromatography (0-20% EtOAc in hexanes) to give the title compound in 72% yield.

Provenance & Evidence