Reaktion #1925200

Reaktionsgleichung

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

Ausbeute 82.0%

Lösungsmittel

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA flask equipped with a stirrer
2. 2
   Temperaturunder reflux for 6.5 hours
3. 3
   FiltrationAfter 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
   Extraktionethyl acetate extraction
7. 7
   ExtraktionThe resulting extract
8. 8
   Waschenwas washed with NaCl saturated water
9. 9
   Trocknendried over anhydrous sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated
12. 12
    Sonstigeto thereby obtain 4.27 g of a crude product in the form of a yellowish brown solid
13. 13
    SonstigeThe crude product was then purified by silica gel column chromatography

Vorschrift

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.

Quelle