Dimethyl Sulfoxide → 9-(1-Propen-1-yl)-9H-carbazole

HRID 1357879

Reaktionsgleichung

Reaktionsgleichung von HRID 1357879
[CH2:1]([N:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:2]=[CH2:3].CC(C)([O-])C.[K+].CS(C)=O>O>[CH:1]([N:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:2][CH3:3]

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 30903939-AllylcarbazoleHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 37533539-(1-Propen-1-yl)-9H-carbazoleAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Into a 100 mL round bottom flask fitted with a magnetic stirrer, reflux condenser and nitrogen inlet were placed 2.07 g (0.01 mole) of 9-allyl carbazole, 1.12 g (0.01 mole) of potassium t-butoxide and 10 mL of DMSO. The reaction mixture was stirred for 20 minutes at room temperature and then was heated to 120° C. and kept at that temperature for two hours. TLC on silica gel was used to monitor the reaction. After cooling to room temperature, the reaction mixture was poured into 20 mL of distilled water and extracted with ethyl ether. The organic layer was washed with distilled water to remove DMSO, then anhydrous sodium sulfate was added and the mixture stirred for an hour. Thereafter, the sodium sulfate was removed by filtration and a rotary evaporator was used to remove the solvent. 9-(1-Propenyl)carbazole was isolated in 63% yield (1.3 g) as a pale yellow viscous liquid. 1H NMR (300 MHz, CDCl3) showed that the product was consisted of approximately a 1:2 ratio of cis and trans 9-(1-propenyl)carbazole isomers.

Aufarbeitung

  1. customInto a 100 mL round bottom flask fitted with a magnetic stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. temperaturewas heated to 120° C.
  4. waitkept at that temperature for two hours
  5. customthe reaction
  6. temperatureAfter cooling to room temperature
  7. extractionextracted with ethyl ether
  8. washThe organic layer was washed with distilled water
  9. customto remove DMSO
  10. additionanhydrous sodium sulfate was added
  11. stirringthe mixture stirred for an hour
  12. customThereafter, the sodium sulfate was removed by filtration
  13. customa rotary evaporator
  14. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-2ee24238f0154a6bb3a39bb0ba86e6e9
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593388B2

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