Potassium Iodide → HCID 11759871, Verbindung

HRID 722686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722686
[C:1]1([CH2:9][OH:10])[CH:6]=[CH:5][C:4]([CH2:7]O)=[CH:3][CH:2]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.C1(C2C=C(F)[CH:34]=[CH:33][C:32]=2[C:38]([C:40]2[CH:45]=[CH:44][C:43](F)=[CH:42][C:41]=2C2CC2)=[O:39])CC1.S(Cl)(Cl)=O.[NH:54]1[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.CC(C)=O>[CH:32]1([C:38]([C:40]2[CH:41]=[CH:42][C:43]([O:10][CH2:9][C:1]3[CH:2]=[CH:3][C:4]([CH2:7][N:54]4[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]4)=[CH:5][CH:6]=3)=[CH:44][CH:45]=2)=[O:39])[CH2:33][CH2:34]1

Komponenten

12

Edukt 8

HCID 4875Potassium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 115061,4-BenzenedimethanolHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 53737258Cyclopropyl-4-fluorophenyl ketone

Produkt 1

HCID 11759871HCID 11759871, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 180AcetoneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution containing 1,4-benzenedimethanol (30 mmol), sodium hydride (25 mmol), catalytic amounts of tetrabutylammonium iodide, and 15-crown-5 (0.5 mmol) in tetrahyrofuran was stirred for 10 minutes. Cyclopropyl-4-fluorophenylketone (20 mmol) was added dropwise, and the solution was refluxed for 24 hours. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: methylene chloride/methanol (98/2)). At 0° C. the product (4 mmol) was added to thionyl chloride (8 mmol). The temperature was raised to 70° C. for three hours. Excess thionyl chloride was evaporated and the residue purified by column chromatography on silica gel (eluent: methylene chloride/methanol (95/5)). The product (2 mmol), piperidine (4 mmol), catalytic amounts of potassium iodide, and potassium carbonate (6 mmol) dissolved in acetone were refluxed for 12 hours. The solvent was evaporated. The crude product was washed with water and extracted with ethyl acetate. The organic layer was removed under reduced pressure. The residue was crystallized with oxalic acid from diethyl ether/ethanol.

Aufarbeitung

  1. temperaturethe solution was refluxed for 24 hours
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: methylene chloride/methanol (98/2))
  4. customExcess thionyl chloride was evaporated
  5. customthe residue purified by column chromatography on silica gel (eluent: methylene chloride/methanol (95/5))
  6. temperaturewere refluxed for 12 hours
  7. customThe solvent was evaporated
  8. washThe crude product was washed with water
  9. extractionextracted with ethyl acetate
  10. customThe organic layer was removed under reduced pressure
  11. customThe residue was crystallized with oxalic acid from diethyl ether/ethanol

Quellen und Nachweise

ORD-Eintrag
ord-047a786019534bf185817b78e9825163
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138413B1

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