Trimethylsilylacetylene → 4-[(Trimethylsilyl)ethynyl]pyridine

HRID 2251962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251962
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])#[CH:10].C(N(C(C)C)CC)(C)C>CN(C=O)C.C(Cl)Cl.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>[CH3:12][Si:11]([C:9]#[C:10][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)([CH3:14])[CH3:13]

Komponenten

8

Edukt 3

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 881004-Bromopyridinium chloride

Produkt 1

HCID 107736004-[(Trimethylsilyl)ethynyl]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Heat a mixture of 4-bromopyridine hydrochloride (1.0 eq), ethynyl-trimethyl-silane (2.0 eq), PdCl2(PPh3)2 (0.1 eq), CuI (0.2 eq) and diisopropyl ethyl amine (10 eq) in DMF at 70° C. for 18 hours. Dilute with methylene chloride, and wash with water. Dry over MgSO4, filter and concentrate in vacuo. Purify the residue by flash chromatography on silica gel to give the title compound. MS (IS) 176.0 (M+1); TLC (20% ether in hexanes): Rf=0.1.

Aufarbeitung

  1. temperatureHeat
  2. washwash with water
  3. dry with materialDry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-32ee18b5a32b49b586301394c3e18a96
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07320994B2

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