Chlorotrimethylsilane → N,1,1,1-Tetramethyl-N-phenylsilanamine

Participants

Reaction Steps

Step 1—To a stirring solution of N-methylaniline (80 g, 0.75 mol) in diethyl ether (600 ml) cooled at −78° C. was added n-butyl lithium (2.4 M in hexanes, 342 ml, 0.82 mol) keeping the temperature below −60° C. The resulting slurry was stirred for 1 hour then chlorotrimethylsilane (114 ml, 0.90 mol) was added while keeping the temperature below −70° C. The reaction was allowed to warm to room temperature overnight then filtered to remove the precipitated white solid. The filtrates were concentrated in vacuo then distilled under high-vac to yield the N-trimethylsilyl-N-methylaniline (126 g, 94%) as a colorless/straw colored liquid: b.p. 48° C./0.6 mmHg; 1H NMR (CDCl3) 0.33 (s, 9H), 2.95 (s, 3H), 6.85 (t, 1H, 7 Hz), 6.94 (d, 2H, 8 Hz), 7.27 (t, 2H, 9 Hz).

Provenance & Evidence