1-Bromododecane → ethyl 1--N-dodecyl-2-pyrrolidone-5-carboxylate

Participants

Reaction Steps

To a stirred solution of 1.92 g NaH (60%, washed with pet ether) in dry THF at room temperature under N2 was added dropwise a solution of 7.06 g of ethyl 2-pyrrolidone-5-carboxylate in 20 mL of THF. The mixture was refluxed for 1 h, cooled to room temperature, followed by dropwise addition of 1.3 equivalents of 1-bromododecane. After additional reflux overnight and workup, the crude oil was subjected to flash chromatography (silica, 8:2 pet ether/EtOAc) to give 3.14 g of ethyl 1--N-dodecyl-2-pyrrolidone-5-carboxylate as a clear oil: NMR (CDCl3) δ 4.2(m), 3.68(m), 2.9(m), 2.6-2.2(m), 2.1(m), 1.6-1.0(m), 0.9(t).

Provenance & Evidence