N,N,N',N'-Tetramethylethylenediamine → N,N-diethyl-2-[(chloromethyl)dimethylsilyl]-1-naphthalenecarboxamide

Participants

Reaction Steps

A solution of 1.3M s-BuLi in cyclohexane (20.3 mL, 26.4 mmol) was added dropwise to an ether/liquid nitrogen-cooled solution of TMEDA (4.0 mL, 26.5 mmol) in THF (15 mL), maintaining the internal reaction temperature <-80° C. To this mixture was added a solution of N,N-diethyl-1-naphthalenecarboxamide (5.0 g, 22.0 mmol) in THF (10 mL), again maintaining the internal reaction temperature <-80° C. The resulting solution was stirred with dry ice/acetone cooling for 30 min, then was recooled to <-80° C. with an ether/liquid nitrogen bath while chloromethyl dimethylsilyl chloride (3.8 mL, 28.8 mmol) was added dropwise. The mixture was warmed to RT to afford a green solution which was diluted with ether and extracted with dilute aq citric acid (2 X), followed with sat aq NaHCO3. The ether solution was dried (MgSO4), concentrated, and chromatographed with 3:17 ethyl acetate/hexanes to afford 4.3 g of N,N-diethyl-2-[(chloromethyl)dimethylsilyl]-1-naphthalenecarboxamide as a yellow oil, a 59% yield.

Provenance & Evidence