Dimethylformamide → 4-Iodo-1-phenethyl-imidazole-2-carbaldehyde

HRID 1773857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773857
[I:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=1.[Li+].CC([N-]C(C)C)C.CN([CH:26]=[O:27])C>C1COCC1>[I:1][C:2]1[N:3]=[C:4]([CH:26]=[O:27])[N:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 867039464-Iodo-1-phenethyl-imidazole

Produkt 1

HCID 867039454-Iodo-1-phenethyl-imidazole-2-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-iodo-1-phenethyl-imidazole (example 2C) (563 mg, 1.89 mmoles) in THF (13 mL) under argon is cooled to −78° C. A 2.0M LDA solution (1.04 mL, 2.08 mmoles) is added dropwise. After 30 minutes at −78° C., DMF (161 μL, 2.08 mmoles) is added dropwise. The reaction mixture is allowed to reach 0° C., then it is quenched by adding a half-saturated NaHCO3 solution. The aqueous phase is extracted three times with AcOEt. The organic phase is washed with water, brine, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (heptane:AcOEt) as eluent with a gradient from (95:5) to (70:30) to give 4-iodo-1-phenethyl-imidazole-2-carbaldehyde.

Aufarbeitung

  1. customto reach 0° C.
  2. customit is quenched
  3. additionby adding a half-saturated NaHCO3 solution
  4. extractionThe aqueous phase is extracted three times with AcOEt
  5. washThe organic phase is washed with water, brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent is removed under reduced pressure
  9. customThe residue is purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-407e33423cf54d29bee1299849f41be2
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255101B2

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