Boron trifluoride etherate → 3-Hydroxy-1-trimethylsilyl-undec-5Z-ene-1-yne

Temperature

-78 °C

Trimethylsilylacetylene (6.9 g, 48.6 mmole) is dissolved in 125 ml dry THF in a flamed dried 500 ml 3-neck round bottom flask under nitrogen at -78° C. The solution is treated with n-butyllithium (29.9 ml, 46.3 mmole) slowly dropwise over 10 minutes and stirred 30 minutes at -78° C. The reaction mixture is subsequently treated slowly dropwise with boron trifluoride etherate (6.0 ml, 48.8 mmole) and the resultant mixture is stirred 20 minutes at -78° C. 3-Z-Nonenal (6.2 g, 44 mmole), in 3×12 ml dry THF, is added rapidly dropwise to the reaction mixture at -78° C. The reaction is warmed to 0° C. and stirred an additional 20 minutes. The mixture is quenched with 100 ml saturated sodium chloride, the layers separated, and the aqueous phase extracted with 3×60 ml diethyl ether. The organics are combined, dried over magnesium sulfate, and concentrated in vacuo to a dark yellow oil (10.5 g). The crude oil is chromatographed over 200 g silica gel (230-400 mesh), eluting with 6% ethyl acetate/hexane and collecting 60 ml fractions. Fractions 8-16 are combined and concentrated to afford 6.3 g of the title compound as a pale yellow oil. Following the above procedure gives the title compound having the physical characteristic described below:

1. customdried 500 ml 3-neck round bottom flask under nitrogen at -78° C
2. temperatureThe reaction is warmed to 0° C.
3. stirringstirred an additional 20 minutes
4. customThe mixture is quenched with 100 ml saturated sodium chloride
5. customthe layers separated
6. extractionthe aqueous phase extracted with 3×60 ml diethyl ether
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated in vacuo to a dark yellow oil (10.5 g)
9. customThe crude oil is chromatographed over 200 g silica gel (230-400 mesh)
10. washeluting with 6% ethyl acetate/hexane
11. customcollecting 60 ml fractions
12. concentrationconcentrated

ORD record

ord-048ed5aca9e940a291b48f8f96303250

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05116981