N,N,N',N'-Tetramethylethylenediamine → HCID 18779202, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-biphenylmethanol (0.368 g, 2 mmol) in ether (25 mL) and TMEDA (1.21 mL, 8 mmol), at 0° C. was added n-butyllithium (2.5N hexanes; 3.2 mL, 8 mmol). The solution was then heated at reflux for 1 h, cooled to -60° C. and CuCN (0.2 g, 2.2 mmol) added. After 30 minutes, the solution was cooled to -78° C. and N-formylpiperidine (1.11 mL, 10 mmol) was then added dropwise and stirring was continued for 1 h. The mixture was then warmed to -10° C., quenched with saturated NH4Cl, extracted with ether washed with brine, dried and the solvent removed in vacuo. Chromatography of the residue (silica gel; hexane:EtOAc 4:1) afforded the title compound as a colorless oil.

Provenance & Evidence