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

HRID 1041832ノート

反応式

HRID 1041832 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6093782Bis(acetonitrile)dichloropalladium触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2869e061967748fa8855941452b23efd
出典データセット
uspto-grants-2013_10
特許番号
US08557142B2

反応ノート

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