Ethanolamine → (2-Aminoethoxy)(tert-butyl)dimethylsilane

Participants

Reaction Steps

tert-Butyldimethylsilylchloride (24.87 g, 165 mmol) was added portion wise to a solution of ethanolamine (11.84 mL, 150 mmol) in triethylamine (46.0 mL, 330 mmol) and dichloromethane (100 mL) at 0° C. The reaction was stirred at this temperature for 1 hour and then allowed to warm to room temperature. After 16 hours, the reaction mixture was washed with sodium hydrogen carbonate solution (2×50 mL) and brine (50 mL), dried over magnesium sulfate, and concentrated in vacuo to give 2-(tert-butyldimethylsilyloxy)ethylamine as a colourless oil. Yield: 24.1 g, 137 mmol, 92%. 1H NMR (400 MHz, CDCl3) δ: 3.63 (2H, t), 2.78 (2H, t), 0.91 (9H, t), 0.07 (6H, s).

Provenance & Evidence