Lithium N‐Benzyltrimethylsilylamide

[113709-50-5] C10H16LiNSi (MW 185.31) InChI = 1S/C10H16NSi.Li/c1-12(2,3)11-9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;/q-1;+1 InChIKey = XMNOZVJUCZKWTB-UHFFFAOYSA-N (less-basic lithium amide capable of regioselective conjugate addition to α,β-unsaturated esters;1 amide cuprates have increased selectivity and reactivity toward enoates2) Alternate Name: LSA. Solubility: sol THF. Preparative Method: to a solution of freshly distilled N-benzyltrimethylsilylamine (0.2 mL, 1.0 mmol)3 in THF at −78 °C is slowly added a solution of n-Butyllithium (0.61 mL, 1.64 M in hexane, 1.0 mmol) under Ar; a pale yellow solution of lithium N-benzyltrimethylsilylamide in THF is obtained after stirring for several min at −78 °C.1 Handling, Storage, and Precautions: is moisture and air-sensitive, and should thus be handled under inert atmosphere; prepare just prior to use; use in a fume hood.