Trimethylsilylmethyl Azide

Experimental procedure⁴⁾: To a solution of veratrole (30 mL, 234 mmol) and N,N,N',N'-tetramethylethylenediamine (35.4 mL, 234 mmol) in ether (240 mL) is added dropwise over 15 min n-butyllithium (2.47 mol/L hexane solution, 94.8 mL, 234 mmol) at 0 °C under an N₂ atmosphere. The resulting suspension is stirred at 22 °C for 18.5 h and then recooled to 0 °C. A solution of trimethylsilylmethyl azide (33.6 mL, 234 mmol) in ether (120 mL) is added dropwise over 10 min into the mixture. The resulting solution is warmed to 22 °C, stirred for an additional 3.5 h, and poured into water (200 mL). The organic layer is extracted with 1 mol/L HCl (5 x 100 mL), and the combined aqueous extracts are made basic to litmus with 3 mol/L NaOH and extracted with ether (5 x 100 mL). The combined ether extracts are washed with water (150 mL), brine (150 mL) and then dried over MgSO₄. Evaporation of the solvent followed by Kugelrohr distillation gives 2,3-dimethoxyaniline (28.3 g, 78% yield).