Imidazole → (But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

Participants

Reaction Steps

To a solution of 3-butyne-1-ol (21.0 g, 0.3 mol) in 100 mL of DMF was added imidazole (41.3 g, 0.6 mol), followed by a solution of t-butyldimethylsilyl chloride (48.0 g, 0.32 mol) in 25 mL of DMF. After stirring at room temperature under Ar for 18 h, the reaction mixture was poured into 10% aqueous NaHCO3 (150 mL) and extracted with hexane (3×250 mL). The organic phase was washed (brine), dried (Na2SO4) and evaporated to give 1-(t-butyl dimethylsiloxy)-3-butyne (49.0 g, 89%) as a colourless oil: IR (neat) 3320, 2125 (w) , 1260, 1110, 840 cm-1 ; 1H NMR (CDCl3, 200 MHz) δ3.74 (t, J=7.2 Hz, 2H), 2.40 (dt, J=7.1, 2.6 Hz, 2H), 1.96 (t, J=2.6 Hz, 1H), 0.90 (s, 9 H), 0.07 (s, 6H).

Provenance & Evidence