Hydrochloric Acid → HCID 86672785, compound

Participants

Reaction Steps

LiOH.H2O (3.8 mg, 0.091 mmol) was added to a solution of 4-(2,2,3,3,3-pentafluoro-propyl)-cyclohexanecarboxylic acid benzyl ester (cis:trans=11:1) (11.4 mg, 0.0325 mmol) in THF (0.15 ml)-H2O (0.15 mL). The mixture was stirred at room temperature for 16 hours, and then adjusted to pH 2 with a 1 N aqueous HCl solution and extracted with dichloromethane. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was dissolved in tert-butanol (0.4 ml), and potassium tert-butoxide (10 mg, 0.089 mmol) was added. The mixture was stirred at room temperature for two hours, and then adjusted to pH 3 with a 1 N aqueous HCl solution and extracted with dichloromethane. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography (hexane/ethyl acetate=5/1) to give 4-(2,2,3,3,3-pentafluoro-propyl)-cyclohexanecarboxylic acid (cis:trans=9:1) (8.5 mg, 100%).

Provenance & Evidence