Trifluoroacetic acid → HCID 68551594, compound

Participants

Reaction Steps

To a solution of (1E,6E)-1,7-bis[5-methoxy-2-(methoxymethoxy)phenyl]hepta-1,6-diene-3,5-dione (14 mg, 31 μmol, synthesized in Example 319) in 1.6 mL of dry dichloromethane was added 0.4 mL of trifluoroacetic acid under nitrogen at 0° C. After being stirred at room temperature for 2 h, the reaction mixture was neutralized with saturated NaHCO3 aqueous solution. The mixture was extracted with ethyl acetate, and the extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 60/40) to obtain (1E,6E)-1,7-bis(2-hydroxy-5-methoxyphenyl)hepta-1,6-diene-3,5-dione (5.0 mg, 44%) and (1E,6E)-1-(2-hydroxy-5-methoxyphenyl)-7-[5-methoxy-2-(methoxymethoxy)phenyl]hepta-1,6-diene-3,5-dione (5.8 mg, 46%) as solids, respectively. (1E,6E)-1-(2-hydroxy-5-methoxyphenyl)-7-[5-methoxy-2-(methoxymethoxy)phenyl]hepta-1,6-diene-3,5-dione (CU456)

Provenance & Evidence