反应详情

温度

-78 °C

n-Butyllithium (3.89 g, 61mmol) in hexane (24.31 mL) was added dropwise to a stirred solution of 1-(1-ethoxyethyl)-2-methyl-4,5-diphenyl-1H-imidazole (l5.50 g, 51 mmol) in dry THF (300 mL) maintained at -78° C. under an atmosphere of nitrogen. The mixture was stirred for 45 minutes and [3-(bromomethyl)-phenoxy]dimethyl(1,1-dimethylethyl)silane (l6.77 g, 50 mmol) added dropwise. After 10 minutes, the mixture was poured onto water, extracted with CH2Cl2, the extracts combined and dried over sodium sulfate. Evaporation of the solvent left an oil which was dissolved in THF (75 mL) and a solution of tetra-n-butylammonium fluoride (l7.22 g, 66mol) in THF (65 mL) added. The solution was stirred at room temperature for 30 minutes, the solvent evaporated and the residue diluted with water. After addition of 2N HCl solution (about 20 mL) to pH=5, the mixture was extracted with CH2Cl 2 The combined extracts were dried over sodium sulfate, concentrated in vacuo and the residual material chromatographed on a column of silica gel. Elution with a mixture of diethyl ether and hexanes (1.0 gave 3-[2-[1-(1-ethoxyethyl)-4,5-diphenyl-1H-imidazol-2-yl]ethyl]-phenol (8.l8 g, 39%), mp 165.5°-167° C. after recrystallization from a mixture of CH2Cl2 and hexanes.

1. waitAfter 10 minutes
2. additionthe mixture was poured onto water
3. extractionextracted with CH2Cl2
4. dry with materialdried over sodium sulfate
5. customEvaporation of the solvent
6. waitleft an oil which
7. dissolutionwas dissolved in THF (75 mL)
8. stirringThe solution was stirred at room temperature for 30 minutes
9. customthe solvent evaporated
10. additionthe residue diluted with water
11. additionAfter addition of 2N HCl solution (about 20 mL) to pH=5
12. extractionthe mixture was extracted with CH2Cl 2 The combined extracts
13. dry with materialwere dried over sodium sulfate
14. concentrationconcentrated in vacuo
15. customthe residual material chromatographed on a column of silica gel
16. washElution
17. additionwith a mixture of diethyl ether and hexanes (1.0