Imidazole → HCID 86748316, compound

Participants

Reaction Steps

To a solution of 10a (2.69 g, crude) and imidazole (5.6 g, 82.3 mmol) in CH2Cl2 (50 mL) was added chlorotriethylsilane (1.7 mL, 10.1 mmol), and the mixture was stirred at ambient temperature overnight. To the mixture were added 2,6-lutidine (1.9 mL, 16.3 mmol) and triethylsilyl trifluoromethanesulfonate (1.9 mL, 8.40 mmol), and the mixture was stirred at ambient temperature for 35 min, then heated under reflux. Heating and stirring were continued with further addition of triethylsilyl trifluoromethanesulfonate (0.8 mL) overnight. Ice was added to the mixture, and the organic layer was separated. The aqueous layer was extracted with n-hexane, and the combined organic layers were washed with cold diluted HCl , water, NaHCO3 solution and NaCl solution, and dried over Na2SO4. Filtration and concentration, followed by chromatographic purification (SiO2 gel 50 g, EtOAc in n-hexane 5%), to give 3.21 g (quantitative yield from 9a) of 11a, as a colorless oil.

Provenance & Evidence