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Trimethylsilylacetylene → 5,5'-Bis(trimethylsilylethynyl)-2,2'-bipyridine

HRID 2176471
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Reaktionsgleichung

Reaktionsgleichung von HRID 2176471
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].Br[C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][N:15]=2)=[N:12][CH:13]=1>C1COCC1.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.[Cu]I>[CH3:1][Si:2]([C:5]#[C:6][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[CH:16][N:15]=2)=[N:12][CH:13]=1)([CH3:4])[CH3:3]
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Komponenten

6

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 109031035,5'-DIBROMO-2,2'-BIPYRIDINE

Produkt 1

HCID 52476625,5'-Bis(trimethylsilylethynyl)-2,2'-bipyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, Verbindung
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under dry nitrogen atmosphere, successively trimethylsilyl-acetylene (619 mg, 6.30 mmol), [Pd(PPh3)2Cl2] (112 mg, 159 mol), CuI (54.5 mg, 286 mol) and DIPA (4 ml) were added to a stirred suspension of 3 (500 mg, 1.59 mmol) in 30 ml THF. While the mixture was stirred for 24 hours at room temperature, its color turned black. It was stirred together with activated carbon for 20 minutes and filtered over celite. Then the solvent was removed under reduced pressure, the residue was resuspended in hexane, sonicated for 15 minutes and filtered over celite again yielding an orange solution. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica (eluent: CH2Cl2) to yield 430 mg (1.23 mmol, 78%) of pure 4 as an off-white solid. 1H NMR (CDCl3, 250 MHz): δ=8.71 (s, 2H, bpy-H), 8.33 (d, 2H, JHH=8.3 Hz, bpy-H), 7.85 (d, 2H, JHH=7.8 Hz, bpy-H), 0.27 (s, 18H, Si(CH3)3).

Aufarbeitung

  1. stirringIt was stirred together with activated carbon for 20 minutes
  2. filtrationfiltered over celite
  3. customThen the solvent was removed under reduced pressure
  4. customsonicated for 15 minutes
  5. filtrationfiltered over celite
  6. customagain yielding an orange solution
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by flash column chromatography on silica (eluent: CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-3705dc103ccc4e03a2051e4952e14356
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09067181B2

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