Cesium carbonate → 2-Cyclohexyl-4-(4-hexylphenylethynyl)-1-(4-propylphenylethynyl)benzene

HRID 1041832노트

반응식

HRID 1041832 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[C:4]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:3]=1.C(C1C=CC(C#C)=CC=1)CC.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[C:53]2[C:58](C(C)C)=[CH:57][C:56]([CH:62](C)[CH3:63])=[CH:55][C:54]=2C(C)C)CCCCC1.O1[CH2:79][CH2:78]OCC1>CC#N.CC#N.Cl[Pd]Cl.O>[CH:17]1([C:4]2[CH:3]=[C:2]([C:63]#[C:62][C:56]3[CH:57]=[CH:58][C:53]([CH2:48][CH2:47][CH2:52][CH2:51][CH2:50][CH3:49])=[CH:54][CH:55]=3)[CH:7]=[CH:6][C:5]=2[C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:78][CH3:79])=[CH:14][CH:15]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

참가 물질

8

반응물 5

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 27751331-Ethynyl-4-propylbenzeneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 670433654-Chloro-2-cyclohexyl-1-p-tolylethynylbenzene

생성물 1

HCID 1236670432-Cyclohexyl-4-(4-hexylphenylethynyl)-1-(4-propylphenylethynyl)benzene

시약·촉매·용매 2

HCID 6093782Bis(acetonitrile)dichloropalladium촉매HCID 962Water용매

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온도
100 °C

실험 절차

4.5 g (11.87 mmol) of 10, 1.7 g (11.87 mmol) of 1-n-propyl-4-ethynyl-benzene, 8.5 g (26.12 mmol) of caesium carbonate, 30 mg (0.1 mmol) of bis(acetonitrile)palladium(II) chloride and 170 mg (0.35 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl are dissolved in 35 ml of dioxane under nitrogen and heated at 100° C. overnight. 100 ml of water are added to the cooled solution, and the mixture is extracted twice with methyl t-butyl ether (100 ml). The combined organic phases are washed with water, dried over sodium sulfate and evaporated in vacuo. The residue is purified by column chromatography, giving the title compound 6 as a solid.

후처리

  1. extractionthe mixture is extracted twice with methyl t-butyl ether (100 ml)
  2. washThe combined organic phases are washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue is purified by column chromatography

출처 및 근거

ORD 기록
ord-2869e061967748fa8855941452b23efd
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557142B2

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