Reacción #81773

Ecuación de reacción

Triphenylphosphonium dibromide

3-octyne-1-ol

→

1-bromo-3-octyne

Rendimiento 96.0%

Disolventes

diethyl ether

—

hexanes

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprecipitated which
2. 2
   Filtraciónwere collected by filtration
3. 3
   OtroThe organic layer was separated
4. 4
   Lavadowashed with 1N aqueous sodium hydroxide, water
5. 5
   Secadodried over magnesium sulfate
6. 6
   FiltraciónThe organic layer was then filtered
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   Otroto give a residue which
9. 9
   Filtraciónfiltered
10. 10
    Otroto remove undissolved material
11. 11
    Concentraciónconcentrated

Procedimiento

Triphenylphosphonium dibromide (36.8 g, 87.2 mmol) was suspended in diethyl ether at -20° C. and a solution of 3-octyne-1-ol (10.0 g, 79.2 mmol) was added dropwise over a twenty minute period. The mixture was allowed to stir overnight. The mixture was poured into ice-water and solids precipitated which were collected by filtration. The organic layer was separated, washed with 1N aqueous sodium hydroxide, water and dried over magnesium sulfate. The organic layer was then filtered and concentrated in vacuo to give a residue which was taken up in hexanes, filtered to remove undissolved material and concentrated to give 1-bromo-3-octyne as an orange oil (14.2 g, 96%). 1H NMR (300 MHZ) spectral data were consistent with the desired bromide (plus a trace of triphenylphosphine), and the crude product was used directly in the next step.

Fuente