3-Cyanopyridine → 3-(Trimethylsilylethynyl)pyridine

HRID 2213975

Reaktionsgleichung

Reaktionsgleichung von HRID 2213975
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#N.[Li].[C-]#[C-].[Li+].[Li+].[CH3:14][Si:15]([C:18]#C)([CH3:17])[CH3:16].C([Li])CCC>C1COCC1.C(#N)C1C=CC=CC=1>[CH3:14][Si:15]([C:18]#[C:1][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)([CH3:17])[CH3:16]

Komponenten

8

Edukt 5

HCID 793-CyanopyridineHCID 66111TrimethylsilylacetyleneHCID 3028194LithiumHCID 178418339ButyllithiumHCID 178462446HCID 178462446, Verbindung

Produkt 1

HCID 41008573-(Trimethylsilylethynyl)pyridineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7505BenzonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The procedure was identical to Example 1, with the exception that 3-cyanopyridine (0.208 g; 2.00 mmol) was used as a substrate instead of benzonitrile and lithium trimethylacetylide (8.00 ml; 4.00 mmol; 0.5 M in THF) was used instead of the in situ derived lithium acetylide made from trimethylsilylacetylene and n-butyllithium. GC analysis of the organic phase of the hydrolyzed reaction sample after 20 h at 65° C. showed the presence of 1.00 mmol (50% yield) of 3-(trimethylsilylethynyl)pyridine and no remaining 3-cyanopyridine in the reaction mixture.

Quellen und Nachweise

ORD-Eintrag
ord-413add957c6c4ebbb468697a624be44e
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105707B2

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