Trifluoroacetic acid → HCID 56969800, compound

HRID 2095988Notes

Reaction equation

HRID 2095988 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8]COC)[CH:5]=[CH:4][C:3]=1[C:12](=[O:23])[CH2:13][CH2:14][C:15]1[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>CC#N.O>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:12](=[O:23])[CH2:13][CH2:14][C:15]1[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67140339HCID 67140339, compound

Product 1

HCID 56969800HCID 56969800, compoundYield 35.8%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(2-hydroxy-4-(methoxymethoxy)phenyl)-3-(6-methoxypyridin-3-yl)propan-1-one (1.62 g, 5.11 mmol) in CH3CN (30 ml) at room temperature was added TFA (2 ml) dropwise, two drops of water. The reaction was stirred at same temperature for 8 h. Aqueous 1N NaOH was added to the reaction mixture until pH=7. The aqueous was extracted with 100 ml EtOAc, and the organic layers were combined. The organic layer was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (15% EtOAc/Hexane) to provide 0.5 g (35%) of white solid.

Workup

  1. extractionThe aqueous was extracted with 100 ml EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (15% EtOAc/Hexane)

Sources & evidence

ORD record
ord-719a993d112a485892385cf2e71d7beb
Source dataset
uspto-grants-2013_05
Patent number
US08449936B2

Reaction notes

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