反应详情

温度

90 °C

1-[1-Triphenylmethyl-1H-imidazol-4-yl]-6-cyclohexyl-3-hexyne (0.629 g, 1.33 mmol) was suspended in ethyl alcohol (3 ml). 2N HCl (25 ml) was added and the reaction mixture heated at 90° C. for 1 hr. The reaction mixture was cooled, filtered through a pad of celite and the filtrate evaporated in vacuo. The residue was dissolved in methanol (20 ml). 10% Pd(C) (0.139 g) and ammonium formate (1.5 g) were added, and the reaction mixture heated at 65° C. under N2 for 6.5 hours. The reaction mixture was cooled, filtered through a pad of celite and the methanol filtrate concentrated. The residue was partitioned between CH2Cl2 and 10% NaOH solution (100 ml, 1:1). The CH2Cl2 layer was separated, washed with water (50 ml), dried over MgSO4, filtered and evaporated in vacuo. Purification by flash chromatography using ethyl acetate as eluent gave 108 mgs of final product. ##STR72## 4-(6-Cyclohexylhexyl)imidazole (41) 1H-NMR (300 MHz, CD3OD): δ7.53 (s, 1H), 6.73 (s, 1H), 2.56 (t, J=7.5 Hz, 2H), 1.65 (m, 7H), 1.40-1.10 (m, 12H), 0.89 (m, 2H); Mass Spectrum: (DCl/NH3): 235 (M+1)+.

1. temperatureThe reaction mixture was cooled
2. filtrationfiltered through a pad of celite
3. customthe filtrate evaporated in vacuo
4. dissolutionThe residue was dissolved in methanol (20 ml)
5. addition10% Pd(C) (0.139 g) and ammonium formate (1.5 g) were added
6. temperaturethe reaction mixture heated at 65° C. under N2 for 6.5 hours
7. temperatureThe reaction mixture was cooled
8. filtrationfiltered through a pad of celite
9. concentrationthe methanol filtrate concentrated
10. customThe residue was partitioned between CH2Cl2 and 10% NaOH solution (100 ml, 1:1)
11. customThe CH2Cl2 layer was separated
12. washwashed with water (50 ml)
13. dry with materialdried over MgSO4
14. filtrationfiltered
15. customevaporated in vacuo
16. customPurification by flash chromatography