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

HRID 403067
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 403067
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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c8d6a1e4633540f19073da98de7a307e
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08747695B2

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