반응 #1925200

반응 방정식

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

수율 82.0%

용매

triethylamine

반응 조건

후처리

1. 1
   기타A flask equipped with a stirrer
2. 2
   온도under reflux for 6.5 hours
3. 3
   여과After 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
   추출ethyl acetate extraction
7. 7
   추출The resulting extract
8. 8
   세척was washed with NaCl saturated water
9. 9
   건조dried over anhydrous sodium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated
12. 12
    기타to thereby obtain 4.27 g of a crude product in the form of a yellowish brown solid
13. 13
    기타The crude product was then purified by silica gel column chromatography

실험 절차

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.

출처