Tetrabutylammonium Fluoride → (5Z)-5-undecen-1-yn-3-ol

Temperature

0 °C

3-Hydroxy-1-trimethylsilyl-undec-5Z-ene-1-yne (6.3 g, 26 mmole) is dissolved in 100 ml dry THF in a flame dried 250 ml one-neck round bottom flask under nitrogen. The solution is cooled to 0° C. and treated slowly dropwise with tetrabutylammonium fluoride (1.0M/THF; 32 ml, 32 mmole). The reaction is stirred one hour at 0° C., quenched with 50 ml 90% saturated sodium chloride, and the THF removed in vacuo. The aqueous residue is extracted with 4×20 ml diethyl ether. The organics are combined, washed with 1×50 ml saturated sodium chloride, and dried over magnesium sulfate. The organics are concentrated in vacuo to a dark amber oil. The crude oil is chromatographed over 100 g silica gel (230-400 mesh), eluting with 8% ethyl acetate/hexane and collecting 20 ml fractions. Fractions 16-39 are combined and concentrated to provide 3.87 g of the title compound as a yellow oil.

1. customdried 250 ml one-neck round bottom flask under nitrogen
2. customquenched with 50 ml 90% saturated sodium chloride
3. customthe THF removed in vacuo
4. extractionThe aqueous residue is extracted with 4×20 ml diethyl ether
5. washwashed with 1×50 ml saturated sodium chloride
6. dry with materialdried over magnesium sulfate
7. concentrationThe organics are concentrated in vacuo to a dark amber oil
8. customThe crude oil is chromatographed over 100 g silica gel (230-400 mesh)
9. washeluting with 8% ethyl acetate/hexane
10. customcollecting 20 ml fractions
11. concentrationconcentrated

ORD record

ord-3d1cf40a2c9d49059ccfc9f521628482

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05116981