Reacción #1925200

Ecuación de reacción

2-(4-{2-[4-bromo-2-(trifluoromethoxy)phenyl]ethynyl}phenoxy)ethanol

5-(4-ethynylphenoxy)pentanol

→

5-{4-[2-(4-{2-[4-(2-hydroxyethoxy)phenyl]ethynyl}-3-(trifluoromethoxy)phenyl)ethynyl]phenoxy}pentane-1-ol

Rendimiento 82.0%

Disolventes

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA flask equipped with a stirrer
2. 2
   Temperaturaunder reflux for 6.5 hours
3. 3
   FiltraciónAfter the insolubles were filtered off
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   workup.ADDITIONethyl acetate was added to the resulting distillate, and the pH
6. 6
   Extracciónethyl acetate extraction
7. 7
   ExtracciónThe resulting extract
8. 8
   Lavadowas washed with NaCl saturated water
9. 9
   Secadodried over anhydrous sodium sulfate
10. 10
    Filtraciónfiltered
11. 11
    Concentraciónconcentrated
12. 12
    Otroto thereby obtain 4.27 g of a crude product in the form of a yellowish brown solid
13. 13
    OtroThe crude product was then purified by silica gel column chromatography

Procedimiento

A flask equipped with a stirrer and a thermometer was charged with 2.99 g (7.44 mmol) of 2-(4-{2-[4-bromo-2-(trifluoromethoxy)phenyl]ethynyl}phenoxy)ethanol and 16 ml of triethylamine under a nitrogen atmosphere. Then 1.52 g (7.44 mmol) of 5-(4-ethynylphenoxy)pentanol, 11.2 mg (0.059 mmol) of copper (I) iodide, 51.5 mg (0.20 mmol) of triphenylphosphine, and 11.2 mg (0.016 mmol) of dichlorobis(triphenylphosphine)palladium were added at room temperature, and stirred under reflux for 6.5 hours. After the insolubles were filtered off and the solvent was distilled off, ethyl acetate was added to the resulting distillate, and the pH was adjusted to an acidity with 1N hydrochloric acid to effect ethyl acetate extraction. The resulting extract was washed with NaCl saturated water, dried over anhydrous sodium sulfate, filtered, and concentrated to thereby obtain 4.27 g of a crude product in the form of a yellowish brown solid. The crude product was then purified by silica gel column chromatography using hexane/ethyl acetate as an eluting solvent to obtain 3.2 g of 5-{4-[2-(4-{2-[4-(2-hydroxyethoxy)phenyl]ethynyl}-3-(trifluoromethoxy)phenyl)ethynyl]phenoxy}pentane-1-ol in the form of a light yellow solid in a 82% yield.

Fuente