반응 #79575

반응 방정식

Imidazole-4-carboxaldehyde

sodium hydride

2-Cyclohexylethyl bromide

→

title compound

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

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도under reflux for 18 hours
3. 3
   기타The cooled mixture was evaporated under reduced pressure
4. 4
   기타the residue was partitioned between water (500 ml) and dichloromethane (500 ml)
5. 5
   기타The layers were separated
6. 6
   건조the organic phase was dried (MgSO4)
7. 7
   기타evaporated under reduced pressure
8. 8
   기타The crude product was purified by column chromatography on silica gel using an elution gradient of toluene:ethyl acetate (100:0 to 96:4)

실험 절차

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 dichloromethane (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+].

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