Chlorotrimethylsilane → HCID 11425908, compound

Participants

Reaction Steps

To a solution of 5.13 g (25 mmol) of N,N,2-triethylbenzamide in THF (50 mL) at -78° C. was added a solution of LDA (Aldrich 2.0M, 15.63 mL, 31.25 mmol). The solution was warmed to -10° C. with ice water over 1 hr, then cooled to -78° C. with dry ice-acetone. TMSCl (6.34 mL, 50 mmol) was added neat at -78° C. and then reaction brought to room temperature after 1 hr. The reaction was quenched with saturated NH4Cl and extracted with ether (2×100 mL), dried over MgSO4, stripped and the residue distilled in a Kugelrohr (130°-140° C., 0.65 mm) to obtain 6.51 g (94%) of N,N-diethyl-2-[1-(trimethylsilyl)ethyl]benzamide.

Provenance & Evidence