Imidazole → HCID 58026139, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 10.6 g (0.032 mol) of 5-fluoro-2-((S)-3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzoic acid and 17.8 g (0.026 mol) of imidazole in 70 mL of DMF was added 75.6 mL (0.45 mol) of TESCl. The reaction mixture was stirred at 100° C. for 3 days. Volatiles were removed in vacuo, the reaction mixture was cooled to 10° C. with an ice bath, and 1 L of 1 N HCl was added. The ice bath was removed and the mixture was stirred at room temperature for 2 hours. Ethyl acetate was added and the mixture was washed with 1 N HCl, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. 200 mL of 1 N HCl is added and stirred for 1 hour. Ethyl acetate was added and the mixture was washed with 1 N HCl, brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford 2-((S)-1,1-dimethyl-3-triethylsilanyloxy-3-trifluoromethylhex-5-ynyl)-5-fluorobenzoic acid.

Provenance & Evidence