Diethylamine → HCID 14716807、化合物

HRID 1655139ノート

反応式

HRID 1655139 の反応式
I[C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.C(N[CH2:12][CH3:13])C.[CH2:14]([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[CH:19][CH:18]=1)[CH2:15][CH3:16]>[Cu](I)I.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.O>[CH2:21]([C:2]1[CH:7]=[CH:6][C:5]([C:24]#[C:23][C:20]2[CH:19]=[CH:18][C:17]([C:14]#[C:15][C:16]3[CH:19]=[CH:18][C:17]([CH2:22][CH2:12][CH3:13])=[CH:14][CH:15]=3)=[CH:22][CH:21]=2)=[CH:4][CH:3]=1)[CH2:20][CH3:23]

参加物

7

反応物 3

HCID 8021DiethylamineHCID 12208p-DiiodobenzeneHCID 27751331-Ethynyl-4-propylbenzene

生成物 1

HCID 14716807HCID 14716807、化合物

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒

実験手順

1,4-Diiodobenzene (2.5 g, 7.57 mmol) was added to diethylamine (80 ml) in nitrogen gas stream, followed by agitating the mixture at room temperature, successively adding copper iodide (60 mg) and dichlorobis(triphenylphosphine)palladium(II) (100 mg), adding 4-propylphenylacetylene (4.37 g, 30 mmol) in several steps, agitating the reaction mixture at room temperature overnight, adding water (200 ml), extracting the resulting deposited crystals with toluene (100 ml), washing the toluene solution with dilute hydrochloric acid, water, an aqueous solution of sodium hydrogen sulfate and water in this order, drying the solution on anhydrous sodium sulfate, passing it through a short column of activated alumina, distilling off toluene and recrystallizing the residue from ethyl acetate to obtain the objective 1,4-bis-(4-propylphenyl-ethynyl)benzene (1.92 g, 5.3 mmol). This product exhibited liquid crystal phases. C-N point: 179.1° C. N-I point: 245.5° C.

後処理

  1. stirringagitating the reaction mixture at room temperature overnight
  2. extractionextracting the resulting
  3. washwashing the toluene solution with dilute hydrochloric acid, water
  4. dry with materialan aqueous solution of sodium hydrogen sulfate and water in this order, drying the solution on anhydrous sodium sulfate
  5. distillationdistilling off toluene
  6. customrecrystallizing the residue from ethyl acetate

出典と根拠

ORDレコード
ord-ac8d1be914834fbd90fab20fe68ec7cf
出典データセット
uspto-grants-1993_10
特許番号
US05250216

反応ノート

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