Iodoethane → HCID 53911617, compound

Participants

Reaction Steps

To a stirred sodium ethoxide solution, freshly prepared with 140 mg of sodium in 30 ml of absolute ethanol, was added 850 mg (3 mmol) of 2-amino-1-(ethoxycarbonylmethyl)-3-methylpyridinium bromide, then the mixture was stirred for 30 min at room temperature. The reaction mixture was treated with 1-(benzyloxycarbonyl)-1-cyano-2-ethoxyethylene (710 mg; 3 mmol) followed by stirred for 30 min at room temperature. The resultant precipitates were collected by filtration, dried, then dissolved in 8 ml of N,N-dimethylformamide (DMF). Ethyl iodide (0.32 ml; 4 mmol) was added to the DMF solution and the mixture was stirred for 2 hours at 60° C. The reaction mixture was cooled at room temperature, extracted with ethyl acetate, the solution was washed with water, dried over anhydrous magnesium sulfate, successively. After removal of the solvent, the residue was chromatographed over silica-gel [eluant: n-hexane-ethyl acetate (1:1)] to give 470 mg (yield: 43%) of the titled compound as yellow needles.

Provenance & Evidence