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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence