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

Participants

Reaction Steps

A stirred, 0° C. solution of homopropargyl alcohol (10 g, 0.14 mol) and tert-butyldimethylsilyl chloride (21.5 g, 0.14 mol) in dichloromethane (50 mL) was treated with triethylamine (22.8 mL, 0.168 mol). The mixture was then stirred overnight at room temperature. The mixture was washed with water and the organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography (95:5 hexane/ethyl acetate) to provide the title compound. 1H NMR (300 MHz, CDCl3): δ 0.08 (s, 6H), 0.90 (s, 9H), 1.96 (t, J=3 Hz, 1H), 2.41 (dt, J=6 Hz, J=3 Hz, 2H), 3.75 (d, J=6 Hz, 2H).

Provenance & Evidence