Water → HCID 70873440, compound

HRID 2172219Notes

Reaction equation

HRID 2172219 reaction equation
I[C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)=[CH:4][CH:3]=1.[F:15][C:16]([F:33])([F:32])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:19][CH:18]=1.CC(C)([O-])C.[Na+].O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[O:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]1[O:6][C:5]1[CH:13]=[CH:14][C:2]([N:29]2[CH2:30][CH2:31][CH:26]([CH2:25][CH2:24][CH2:23][C:20]3[CH:19]=[CH:18][C:17]([C:16]([F:15])([F:32])[F:33])=[CH:22][CH:21]=3)[CH2:27][CH2:28]2)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 29168032H-Pyran, tetrahydro-2-(4-iodophenoxy)-HCID 23676156Sodium t-butoxideHCID 69553293HCID 69553293, compound

Product 1

HCID 70873440HCID 70873440, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 44558591Tri-t-butylphosphine fluoroborateCatalystHCID 1140TolueneSolvent

Procedure

2-(4-Iodophenoxy)tetrahydropyran (1.12 g, 3.7 mmol) and 4-[3-(4-trifluoromethylphenyl)propyl]piperidine (1 g, 3.7 mmol) were dissolved in degassed anhydrous toluene (10 ml). Sodium tert-butoxide (0.50 g, 5.2 mmol), tri-tert-butylphosphine tetrafluoroborate (tBu3P.HBF4) (0.09 g, 0.3 mmol) and palladium acetate (0.03 g, 0.15 mmol) were added thereto, and the mixture was heated at reflux under a nitrogen atmosphere for 5 hours. After being allowed to cool to room temperature, water (10 ml) was added to the mixture, followed by extraction with ethyl acetate. The organic layers were combined and washed with water and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. After removing insoluble matter by filtration, the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20) to afford the title compound as a pale yellow solid (1.42 g, 86%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under a nitrogen atmosphere for 5 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashed with water
  5. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
  6. customAfter removing insoluble matter
  7. filtrationby filtration
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20)

Sources & evidence

ORD record
ord-139ad16ffecc460386d756a67bcb1d8d
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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