Hydrochloric Acid → HCID 86594542, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2E,4E,6Z)-8,8,8-trifluoro-7-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-octa-2,4,6-trienoic acid ethyl ester (Intermediate 5, 100 mg, 0.23 mmol) in EtOH-THF-H2O (2 mL, 2 mL, 0.3 mL) was added LiOH.H2O 29 mg, 0.69 mmol). The mixture was heated to 40° C. for 4 h and was cooled to ambient temperature, acidified with 1M HCl and extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (40% EtOAc-hexane) to give a 3:2 mixture of the title compound and its 13-Z isomer (91 mg). Further purification by HPLC (20% EtOAc-hexane) afforded the title compound as a white solid (39 mg, 42%).

Provenance & Evidence