Ethanol → HCID 57809733, compound

HRID 2106027Notes

Reaction equation

HRID 2106027 reaction equation
[O:1]1CCCO[CH:2]1[C:7]1[CH:8]=[C:9]([C:13]([CH3:34])([CH3:33])[CH2:14][C:15]([OH:32])([C:28]([F:31])([F:30])[F:29])[CH2:16][N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20](=[O:27])[CH:19]=[CH:18]2)[CH:10]=[CH:11][CH:12]=1.C(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1>O>[F:31][C:28]([F:29])([F:30])[C:15]([OH:32])([CH2:16][N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])[CH:19]=[CH:18]1)[CH2:14][C:13]([C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[CH:2]=[O:1])([CH3:33])[CH3:34]

Participants

5

Reactant 3

HCID 702EthanolHCID 22033616Pyridinium.p-toluenesulfonateHCID 57809880HCID 57809880, compound

Product 1

HCID 57809733HCID 57809733, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-[4-(3-[1,3]dioxan-2-ylphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (0.99 g, 2.09 mmol), ethanol (66 mL), water (13.2 mL), and pyridinium p-toluenesulfonic acid (262 mg, 1.04 mmol) was heated at reflux for 3 hours, cooled to room temperature and concentrated in vacuo to remove ethanol. The residue was diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, and dried over sodium sulfate. Removal of the volatile in vacuo afforded 3-[4,4,4-trifluoro-3-hydroxy-1,1-dimethyl-3-(4-oxo-4H-quinolin-1-ylmethyl)butyl]benzaldehyde. Yield: 77 mg (89%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated in vacuo
  4. customto remove ethanol
  5. additionThe residue was diluted with ethyl acetate and water
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate and brine
  8. dry with materialdried over sodium sulfate
  9. customRemoval of the volatile in vacuo

Sources & evidence

ORD record
ord-c717698172a645b8b3b4c9675da597fa
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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