Trifluoroacetic acid → HCID 68551594, compound

HRID 1854689Notes

Reaction equation

HRID 1854689 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:30]COC)=[C:7](/[CH:9]=[CH:10]/[C:11](=[O:29])[CH2:12][C:13](=[O:28])/[CH:14]=[CH:15]/[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[O:24][CH2:25][O:26][CH3:27])[CH:8]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[OH:24][C:17]1[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:16]=1/[CH:15]=[CH:14]/[C:13](=[O:28])[CH2:12][C:11](=[O:29])/[CH:10]=[CH:9]/[C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[OH:30].[OH:30][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=1/[CH:9]=[CH:10]/[C:11](=[O:29])[CH2:12][C:13](=[O:28])/[CH:14]=[CH:15]/[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[O:24][CH2:25][O:26][CH3:27]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68554592HCID 68554592, compound

Product 2

HCID 68551594HCID 68551594, compoundYield 46%HCID 68553793HCID 68553793, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 60/40)

Sources & evidence

ORD record
ord-7b3133bb26a64a6db0480bad2ce86114
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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