Acetone → HCID 86594540, compound

Participants

Reaction Steps

A mixture 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, 160 mg, 0.37 mmol), K2CO3 (253 mg, 1.83 mmol), MeI (0.12 mL, 1.83 mmol), and acetone (2 mL), was stirred at ambient temperature for overnight. The reaction mixture was diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (3% EtOAc-hexane) to produce the title compound and its 2-Z isomer as a 2:1 mixture (167 mg). Further purification by HPLC (2.5% EtOAc-hexane) afforded the title compound as a clear oil (87 mg, 53%).

Provenance & Evidence