Ethanol → HCID 86759444, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2E,4E,6E)-7-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-6-fluoro-3-methyl-octa-2,4,6-trienoic acid ethyl ester (Compound 24, 117 mg, 2.74 mmol) and 5 ml of ethanol and 1 ml of THF was added 2 ml of 1 M NaOH(aq). The reaction was heated to 50° C. for 4 hours. The excess alcohol was removed by evaporation. The residue was neutralized with saturated NH4Cl to pH=7 then extracted with ethyl acetate (3×10 ml). The combined organic layers were washed with water, and brine, dried over Na2SO4 and concentrated to give the crude acid as a residue. This was purified by column chromatography (silica, first using 100% hexane, followed by 5:95 ethyl acetate:hexane, then 1:1 ethyl acetate:hexane) to yield a yellow oil. The resulting yellow oil was recrystallized from acetonitrile to produce the title compound as a yellow solid.

Provenance & Evidence