Triethylamine → 3-Fluoro-4-methylpyridine-2-carbonitrile

HRID 1281902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1281902
[F:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH2:10]([N:12](CC)CC)C.C[Si](C#N)(C)C>C(#N)C>[C:10]([C:3]1[C:2]([F:1])=[C:7]([CH3:8])[CH:6]=[CH:5][N:4]=1)#[N:12]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 184233593-Fluoro-4-methylpyridine 1-oxide

Produkt 1

HCID 184233523-Fluoro-4-methylpyridine-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of 0.95 g (7.48 mmol) of 3-fluoro-4-methylpyridine N-oxide 5-2 in 20 mL of acetonitrile was added 1.14 g (11.2 mmol) of triethylamine followed by 1.48 g (15.0 mmol) of trimethylsilyl cyanide. This reaction mixture was heated at reflux for 48 h, after which time the solution was concentrated at reduced pressure. The dark residue was dissolved in CHCl3, washed with saturated aqueous NaHCO3 and the aqueous layer back-washed with chloroform (4×). The combined organic layers were dried over MgSO4 and the solvents removed at reduced pressure to give an oil that was chromatographed on SiO2 using 75:25 hexane-EtOAc to give 5-3 as a yellow oil: 1H NMR (CDCl3) δ 8.39 (d, 1H, 4.8 Hz), 7.09 (br dd, 1H, 5.8, 5.8 Hz), 2.41 (s, 3H).

Aufarbeitung

  1. temperatureThis reaction mixture was heated
  2. temperatureat reflux for 48 h
  3. concentrationafter which time the solution was concentrated at reduced pressure
  4. dissolutionThe dark residue was dissolved in CHCl3
  5. washwashed with saturated aqueous NaHCO3
  6. washthe aqueous layer back-washed with chloroform (4×)
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. customthe solvents removed at reduced pressure
  9. customto give an oil that
  10. customwas chromatographed on SiO2 using 75:25 hexane-EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-1e23d021ca6341a6b664cde5ff9032e8
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06455532B1

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