Hydrochloric Acid → HCID 66817213, compound

Participants

Reaction Steps

A 1 N aqueous NaOH solution (0.084 ml, 0.084 mmol) was added to a solution of 4-(3,3-difluoro-allyl)-cyclohexanecarboxylic acid benzyl ester (trans:cis=4:1) (14.1 mg, 0.0478 mmol) in methanol (1.0 mL). The mixture was stirred at room temperature for 1.5 hours, and then adjusted to pH 6 with a 1 N aqueous HCl solution and concentrated under reduced pressure. The resulting residue was adjusted to pH 3 with dilute hydrochloric acid and extracted with dichloromethane, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was dissolved in THF (0.2 ml)-H2O (0.2 ml), and LiOH.H2O (7.7 mg, 0.18 mmol) was added. The mixture was stirred at room temperature for three 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) to give 4-(3,3-difluoro-allyl)-cyclohexanecarboxylic acid (8.3 g, 86%).

Provenance & Evidence