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

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%).

1. customquenched by addition of saturated aq. NH4Cl (50 ml)
2. extractionThe mixture was extracted with Et2O (3×40 ml)
3. washthe combined organic phases were washed with brine (50 ml)
4. dry with materialbefore being dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customto give the crude product
8. customThis was purified by column chromatography on silica
9. washeluting with petrol/Et2O (10:1 to 9:1)

ORD record

ord-b6d2b76bd6ce4bd89dc90191eeb12939

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242954B2