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Water → 1-(4-n-Butylphenylethynyl)-4-(4-n-propylphenylethynyl)naphthalene

HRID 403067
ノート
印刷プレビュー

反応式

HRID 403067 の反応式
BrC1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][CH:15]=2)=[CH:4]C=1.[CH2:23]([C:27]1[CH:32]=[CH:31][C:30]([C:33]#[CH:34])=[CH:29][CH:28]=1)[CH2:24][CH2:25][CH3:26].O.[CH3:36][CH2:37]CCCCC>CCN(CC)CC.[Cu]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>[CH2:33]([C:30]1[CH:29]=[CH:28][C:27]([C:23]#[C:24][C:25]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][CH3:22])=[CH:18][CH:19]=3)=[CH:4][CH:26]=2)=[CH:32][CH:31]=1)[CH2:34][CH2:36][CH3:37]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 962WaterHCID 8900HeptaneHCID 27751321-Butyl-4-ethynylbenzeneHCID 671178511-Bromo-4-(4-n-propylphenylethynyl)naphthalene

生成物 1

HCID 867624711-(4-n-Butylphenylethynyl)-4-(4-n-propylphenylethynyl)naphthalene

試薬・触媒・溶媒 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 178418476HCID 178418476、化合物触媒
HCID 8471Triethylamine溶媒

実験手順

2.35 g (6.3 mmol) of 1-bromo-4-(4-n-propylphenylethynyl)naphthalene and 1.33 g (8.4 mmol) of 4-n-butylphenylacetylene are initially introduced in 40 ml of NEt3, 60 mg (0.3 mmol) of copper(I) iodide and 200 mg (0.3 mmol) of bis(triphenylphosphine)palladium(II) chloride are added, and the mixture is refluxed for 18 h. The batch is cooled, water and heptane are added, and the phases are separated. The organic phase is washed with saturated ammonium chloride solution and subsequently with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in a rotary evaporator. The residue of compound (1) is purified by column chromatography (SiO2, heptane), and the further purification is carried out by recrystallisation from isopropanol.

後処理

  1. temperaturethe mixture is refluxed for 18 h
  2. temperatureThe batch is cooled
  3. customthe phases are separated
  4. washThe organic phase is washed with saturated ammonium chloride solution and subsequently with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in a rotary evaporator
  8. customThe residue of compound (1) is purified by column chromatography (SiO2, heptane)
  9. customthe further purification
  10. customis carried out by recrystallisation from isopropanol

出典と根拠

ORDレコード
ord-c8d6a1e4633540f19073da98de7a307e
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08747695B2

反応ノート

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