تفاعل #1144443

معادلة التفاعل

4-Pentylphenylacetylene

4-acetoxyphenyl iodide

toluene

→

4-(4′-Pentylphenyl)ethynyl phenol

المذيبات

diisopropylamine

ظروف التفاعل

المعالجة

1. 1
   أخرىevaporated 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
   أخرىThe mixture was evaporated to dryness
5. 5
   أخرىpartitioned between ethyl acetate and water
6. 6
   أخرىthe organic phase was removed
7. 7
   أخرىdried
8. 8
   أخرىevaporated
9. 9
   أخرىThe residue was purified by flash column chromatography
10. 10
    workup.WAITA pink coloured solid was left
11. 11
    أخرىafter evaporation of the appropriate fractions
12. 12
    أخرى1H-NMR and IR spectroscopy gave the expected signals

الإجراء التجريبي

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.

المصدر