Tetrahydrofuran → HCID 70873568, compound

HRID 2172242Notes

Reaction equation

HRID 2172242 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:28][C:29]([Si](C)(C)C)([F:31])[F:30].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][C:24]([C:29]([F:31])([F:30])[F:28])([OH:27])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 70873709HCID 70873709, compound

Product 1

HCID 70873568HCID 70873568, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 82707Tetrabutylammonium AcetateCatalystHCID 962WaterSolvent

Procedure

1-(4′-Benzyloxybiphenyl-4-yl)piperidin-4-one (7.1 g, 19.9 mmol), tetrabutylammonium acetate (0.3 g, 1.0 mmol) and 1,2-dimethoxethane (100 ml) were mixed. While stirring the mixture under ice cooling, trifluoromethyltrimethylsilane (4.11 ml, 27.8 mmol) was added to the mixture and warmed to room temperature, followed by stirring for 6 hours. The residue obtained by distilling off the solvent was dissolved in tetrahydrofuran (100 ml). While stirring at room temperature, 1 mol/l tetrabutylammonium fluoride in tetrahydrofuran (23.8 ml, 23.8 mmol) was added thereto and stirred at room temperature overnight. Water was added to the residue obtained by distilling off the solvent, followed by extraction with dichloromethane. The organic layer was washed with water and dried over sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The resulting crude crystal was washed with diethylether to afford the title compound as a white powder (7.6 g, yield 90%).

Workup

  1. stirringby stirring for 6 hours
  2. customThe residue obtained
  3. distillationby distilling off the solvent
  4. dissolutionwas dissolved in tetrahydrofuran (100 ml)
  5. stirringWhile stirring at room temperature
  6. stirringstirred at room temperature overnight
  7. customobtained
  8. distillationby distilling off the solvent
  9. extractionfollowed by extraction with dichloromethane
  10. washThe organic layer was washed with water
  11. dry with materialdried over sodium sulfate
  12. filtrationAfter filtering
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. washThe resulting crude crystal was washed with diethylether

Sources & evidence

ORD record
ord-8042cf97b43a47cd8d886d8f61f1375b
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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