(2-Bromoethyl)cyclohexane → 1-(2-Cyclohexylethyl)-1H-imidazole-4-carboxaldehyde

HRID 968426

Reaktionsgleichung

Reaktionsgleichung von HRID 968426
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1.[H-].[Na+].[CH:10]1([CH2:16][CH2:17]Br)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCCC1>[CH:10]1([CH2:16][CH2:17][N:1]2[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

5

Edukt 3

HCID 15440(2-Bromoethyl)cyclohexaneHCID 24758Sodium hydrideHCID 764281H-Imidazole-4-carbaldehyde

Produkt 1

HCID 222898451-(2-Cyclohexylethyl)-1H-imidazole-4-carboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Imidazole-4-carboxaldehyde (4.8 g, 50 mmol) was added portionwise to a suspension of sodium hydride (2.20 g, 60% dispersion in mineral oil, 55 mmol) in tetrahydrofuran (150 ml), and the mixture was then stirred at room temperature for 1 hour. 2-Cyclohexylethyl bromide (8.6 ml, 55 mmol) was added, and the mixture was heated under reflux for 18 hours. The cooled mixture was evaporated under reduced pressure and the residue was partitioned between water (500 ml) and dichlorornethane (500 ml). The layers were separated, and the organic phase was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of toluene:ethyl acetate (100:0 to 96:4) to afford the title compound, 1.78 g. 1H-NMR (CDCl3, 400 MHz) δ: 0.98 (m, 2H), 1.20 (m, 4H), 1.68 (m, 7H), 4.00 (t, 2H), 7.4 (s, 1H), 7.60 (s, 1H), 9.80 (s, 1H). LRMS: m/z (TSP+) 207.2 [MH+].

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customThe cooled mixture was evaporated under reduced pressure
  4. customthe residue was partitioned between water (500 ml) and dichlorornethane (500 ml)
  5. customThe layers were separated
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel using an elution gradient of toluene:ethyl acetate (100:0 to 96:4)

Quellen und Nachweise

ORD-Eintrag
ord-3263265a98ea4ec28407b509f546df5c
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06958402B2

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