Hydrochloric Acid → (S)-2-((R)-2-(4-Fluoro-3-methylphenyl)-2-hydroxyethyl)pent-4-enoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 150 mg (3S,5R)-3-allyl-5-(4-fluoro-3-methylphenyl)dihydrofuran-2(3H)-one in 5 mL dioxane was added 5 mL aq. 5% KOH at 25° C. The mixture was stirred for 30 min at 25° C. then hydrolyzed with 10 mL of 1M HCl. The resulting mixture was extracted twice with ethyl acetate (10 mL). The combined organic layers were then extracted with 5 mL 5% K2CO3 three times and the combined aqueous layers acidified with 1M HCl to pH3. The resulting mixture was extracted with ethyl acetate (3×30 mL), the combined organic layers washed with brine (2×20 mL) before being concentrated under reduced pressure. The crude product residue was used for the next step without further purification.

Provenance & Evidence