Sodium Azide → 2-(2-(2-Azidoethoxy)ethoxy)ethanol

Participants

Reaction Conditions

Reaction Steps

In a 250 mL flask, 2-[2-(2-chloroethoxy)ethoxy]ethanol (1) (6000 mg, 35.7 mmol), NaN3 (6964 mg, 107 mmol) and tetrabutylammonium iodide (TBAI) (656 mg, 1.7 mmol) were added to 80 mL DMF. The temperature was slowly raised to 120° C. and the reaction mixture was stirred under argon overnight. The solvent was evaporated and the residue was purified by FCC to afford 2 as slightly yellow oil (4150 mg, 66%). 1H NMR (400 MHz, CDCl3): δ 3.29 (t, J=5.2 Hz, 2H), 3.50 (m, 2H), 3.57-3.64 (m, 8H). 13C NMR (100 MHz, CDCl3): δ 50.59, 61.60, 69.98, 70.34, 70.59, 72.56.

Provenance & Evidence