Toluene → 4-[(4-Pentylphenyl)ethynyl]phenol

HRID 1057261

반응식

HRID 1057261 반응식
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[CH:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C([O:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1)(=O)C.C1(C)C=CC=CC=1>C(NC(C)C)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][C:21]2[CH:20]=[CH:19][C:18]([OH:17])=[CH:23][CH:22]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

참가 물질

7

반응물 3

HCID 1140TolueneHCID 1417934-IodophenylacetateHCID 27751311-Ethynyl-4-pentylbenzene

생성물 1

HCID 186711384-[(4-Pentylphenyl)ethynyl]phenol

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 7912Diisopropylamine용매

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.

후처리

  1. customevaporated to dryness on a rotary evaporator
  2. dissolutionThe residue was redissolved in aqueous potassium hydroxide ethanolic solution
  3. stirringstirred at 70° C. overnight
  4. customThe mixture was evaporated to dryness
  5. custompartitioned between ethyl acetate and water
  6. customthe organic phase was removed
  7. customdried
  8. customevaporated
  9. customThe residue was purified by flash column chromatography
  10. waitA pink coloured solid was left
  11. customafter evaporation of the appropriate fractions
  12. custom1H-NMR and IR spectroscopy gave the expected signals

출처 및 근거

ORD 기록
ord-fbc96aea378f44dca8347db3b9ca696d
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514578B1

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