3-[2-(2-iodoethoxy)ethoxy]prop-1-yne

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To tert-butyl 4-hydroxyphenylcarbamate (1.675 g, 8.01 mmol) in DMF (53.4 mL) was added 3-(2-(2-iodoethoxy)ethoxy)prop-1-yne (2.034 g, 8.01 mmol) and K2CO3 (3.32 g, 24.02 mmol). The mixture was stirred at 60° C. for 4 hours followed by the addition of saturated sodium bicarbonate. The mixture was then extracted with ethyl acetate twice, dried over MgSO4, filtered, and then concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% ethyl acetate/heptane) giving tert-butyl 4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)-phenylcarbamate (I-7a: 1.91 g, 71%) as a colorless oil. LC-MS (M-tBu+1) 280.1, t=1.31 minute. The mixture was then extracted with ethyl acetate twice dried over MgSO4 filtered concentrated in vacuo The residue was purified by silica gel chromatography (0-40% ethyl acetate/heptane)