Potassium Iodide → (4-Iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

HRID 132990

Reaktionsgleichung

Reaktionsgleichung von HRID 132990
[C:1]([O:4][CH2:5][C:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2].FC(F)(F)C([O-])=O.[Tl+].[I-:30].[K+].C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O.O.C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[O:21])[C:10]=2[C:9]([I:30])=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 21902506Thallium(1+);2,2,2-trifluoroacetateHCID 58646841(5-Oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

Produkt 1

HCID 12150904(4-Iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4.4 g of (5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate prepared in Example 1-f was dissolved in 30 ml of trifluoroacetic acid, and 5.0 g of thallium trifluoroacetate was added at room temperature in an atmosphere of nitrogen gas. The mixture was stirred at room temperature for 4 hours, followed by stirring at 50° C. for 2 hours. After the starting material disappeared, 3 ml of an aqueous solution of 1.5 g of potassium iodide was added to the reaction mixture and the mixture was stirred at room temperature for 0.5 hour. To the reaction mixture were added ethyl acetate and water, and the mixture was neutralized with sodium hydrogencarbonate and filtered through Celite. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:20), to give 4.1 g of a 3:1 mixture of the title compounds as a colorless oil.

Aufarbeitung

  1. stirringby stirring at 50° C. for 2 hours
  2. stirringthe mixture was stirred at room temperature for 0.5 hour
  3. filtrationfiltered through Celite
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified
  8. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:20)
  9. customto give

Quellen und Nachweise

ORD-Eintrag
ord-beb1bafe3a1c4769af44e738bbebdf18
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390797B2

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