반응 #1144443

반응 방정식

4-Pentylphenylacetylene

4-acetoxyphenyl iodide

toluene

→

4-(4′-Pentylphenyl)ethynyl phenol

용매

diisopropylamine

반응 조건

후처리

1. 1
   기타evaporated to dryness on a rotary evaporator
2. 2
   workup.DISSOLUTIONThe residue was redissolved in aqueous potassium hydroxide ethanolic solution
3. 3
   workup.STIRRINGstirred at 70° C. overnight
4. 4
   기타The mixture was evaporated to dryness
5. 5
   기타partitioned between ethyl acetate and water
6. 6
   기타the organic phase was removed
7. 7
   기타dried
8. 8
   기타evaporated
9. 9
   기타The residue was purified by flash column chromatography
10. 10
    workup.WAITA pink coloured solid was left
11. 11
    기타after evaporation of the appropriate fractions
12. 12
    기타1H-NMR and IR spectroscopy gave the expected signals

실험 절차

4-Pentylphenylacetylene (10.5 g, 61.4 mmol), 4-acetoxyphenyl iodide (16.1 g, 61.4 mmol), a catalytic amount of Pd(PPh3)2Cl2 and a catalytic amount of copper iodide were stirred in diisopropylamine (100 ml) at 70° C. After 5 minutes, a precipitate was seen and the mixture became unstirrable, toluene (100 ml) was added. The mixture was stirred at room temperature for 24 hours and then evaporated to dryness on a rotary evaporator. The residue was redissolved in aqueous potassium hydroxide ethanolic solution and stirred at 70° C. overnight. The mixture was evaporated to dryness, then partitioned between ethyl acetate and water, the organic phase was removed, dried and evaporated. The residue was purified by flash column chromatography using DCM as eluant. A pink coloured solid was left after evaporation of the appropriate fractions. Yield=10.4 g, 64%. 1H-NMR and IR spectroscopy gave the expected signals.

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