Water → 5,5-dimethyl-5H-indeno[1,2-b]pyridine

HRID 578604

Reaktionsgleichung

Reaktionsgleichung von HRID 578604
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2CC3[C:13]([C:2]=12)=[CH:12][CH:11]=[CH:10][CH:9]=3.[CH3:14][C:15]([CH3:18])([O-])[CH3:16].[K+].IC.O>O1CCCC1>[CH3:14][C:15]1([CH3:18])[C:3]2[C:2](=[N:1][CH:6]=[CH:5][CH:4]=2)[C:13]2[C:16]1=[CH:9][CH:10]=[CH:11][CH:12]=2

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 92054-AzafluoreneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 578727185,5-dimethyl-5H-indeno[1,2-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

13.5 g (80.7 mmol) of 5H-indeno[1,2-b]pyridine was dissolved in 120 ml dry tetrahydrofuran, and 22.7 g (202 mmol) of potassium tert-butoxide was added to the solution at −10° C. The reaction mixture was maintained at −10° C. for 1 hour. Then the iodomethane 28.7 g (202 mmol) was added dropwise; the solution was then warmed slowly to room temperature and stirred for 6 h. After the reaction completion, water was added to the mixture to terminate the reaction. The reaction mixture was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuo, and the residue was crystallized with toluene to give the 5,5-dimethyl-5H-indeno[1,2-b]pyridine, 13.5 g (86%)

Aufarbeitung

  1. temperaturethe solution was then warmed slowly to room temperature
  2. customto terminate
  3. customthe reaction
  4. extractionThe reaction mixture was extracted with ethyl acetate and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customthe residue was crystallized with toluene

Quellen und Nachweise

ORD-Eintrag
ord-b3894a2cf5fc47afa0d00ce4fbf00472
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040174B2

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