1-Bromododecane → 1-Dodecylazacyclohept-3-ene-2-one

Participants

Reaction Steps

A solution of 11.4 g (0.102 mol) of a mixture of azacyclohept-3-ene-2-one and azacyclohept-4-ene-2-one in THF was added dropwise to a suspension of 4.8 g (107 mmol) of sodium hydride (50% oil dispersion) in THF. The mixture was stirred at room temperature for 1 hour, 25.4 g (0.102 mol) of dodecyl bromide was added, and the solution was refluxed for 5 hours. The mixture was cooled, water was added, and the solvent was removed in vacuo. The residue was dissolved in CH2Cl2, washed with water, the organic phase dried over MgSO4 and concentrated in vacuo to yield an oil which was Kugelrohr distilled to give 15.5 g of crude product. This material was subjected to flash chromatography (silica gel; 9:1 petroleum ether/ether V/V) to give 1-dodecylazacyclohept-3-ene-2-one, Rf =0.5, GC (column: 48 inch, 2% OV 101; conditions: injector, detector 320° C., program; 140° C. for 3 min, then to 190° C. in 30° C./min) GC retention time, 7.74 min.

Provenance & Evidence