Dimethylformamide → 2-Formyl-1-methyl-4-phenyl-5-[4-pyridyl]imidazole

HRID 1387643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1387643
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:4]=[CH:3]1.C([Li])CCC.CN([CH:27]=[O:28])C>C1COCC1>[CH:27]([C:3]1[N:2]([CH3:1])[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:4]=1)=[O:28]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 187714831-Methyl-4-phenyl-5-(4-pyridyl)imidazoleHCID 178418339Butyllithium

Produkt 1

HCID 187715342-Formyl-1-methyl-4-phenyl-5-[4-pyridyl]imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-methyl-4-phenyl-5-[4-pyridinyl]imidazole (0.275 g, 1.17 mmol) in THF at −78° C. was added n-butyllithium (0.56 mL of 2.5 M solution, 1.40 mmol). The resulting red-orange solution was allowed to stir at −78° C. for 0.5 h when DMF (0.18 mL, 2.34 mmol) was added. The mixture was allowed to warm to rt and stir for 4 h, then quenched with ice water and partitioned between CH2Cl2 and H2O. The organic extract was washed with aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo and the residue was purified by flash chromatography eluting with 50:1 CH2Cl2/MeOH. The title compound was obtained as a white solid (0.187 g, 61%): mp 167-168° C.

Aufarbeitung

  1. additionwas added
  2. customquenched with ice water
  3. custompartitioned between CH2Cl2 and H2O
  4. extractionThe organic extract
  5. washwas washed with aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by flash chromatography
  9. washeluting with 50:1 CH2Cl2/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-5b37d963f57845878e28b54286b73595
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06268370B1

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