Potassium Carbonate → Tert-butyl 4-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)phenylcarbamate

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl 4-hydroxyphenylcarbamate (1.24 g, 5.93 mmol), 2-(2-(2-azidoethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (1.50 g, 4.56 mmol) and K2CO3 (2.45 g, 17.79 mmol) in acetonitrile was stirred at 80° C. overnight. The reaction mixture was filtered and washed with acetonitrile. After the solvent was evaporated, the reaction mixture was diluted with DCM. The DCM solution was washed with sat. K2CO3 aqueous solution and brine. The organic phase was dried, and concentrated in vacuo to afford tert-butyl 4-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)phenylcarbamate (1.88 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.26 (d, J=8.8 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 6.35 (s, 1H), 4.10 (t, J=4.8 Hz, 2H), 3.85 (t, J=4.8 Hz, 2H), 3.76-3.62 (m, 6H), 3.39 (t, J=5.2 Hz, 2H), 1.52 (s, 9H); MS (ESI), 389 (M+Na)+.

Provenance & Evidence