Tetrabutylammonium Fluoride → (S)-5-Phenylpent-1-yn-3-ol

Participants

Reaction Steps

Following a modified procedure of Trost (Trost, B. M. et al., J. Am. Chem. Soc. 128, 6745-6754 (2006)); Tetrabutylammonium fluoride (1.0 M in THF, 25 ml, 25 mmol, 2.5 eq.) was added to a solution of (S)-5-phenyl-1-(triisopropylsilyl)pent-1-yn-3-ol 85 (3.165 g, 10 mmol, 1 eq.) in THF (95 ml). The reaction mixture was stirred for 1 h at r.t. and then quenched by addition of saturated aq. NH4Cl (50 ml). The mixture was extracted with Et2O (3×40 ml), the combined organic phases were washed with brine (50 ml) before being dried (MgSO4), filtered and concentrated to give the crude product. This was purified by column chromatography on silica, eluting with petrol/Et2O (10:1 to 9:1), giving the title product 86 as a clear, colourless oil (1.6 g, 99%).

Provenance & Evidence