Ethanol → 6-Chloro-1,2,3,4-tetrahydrocarbazole

HRID 1978277

Reaktionsgleichung

Reaktionsgleichung von HRID 1978277
[Cl:1][C:2]1C=C[C:5]([NH:8]N=C(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][CH:3]=1.[C:23]1(=O)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.CC1C=CC(S(O)(=O)=O)=CC=1.O.C([O-])(O)=O.[Na+].[CH2:47](O)[CH3:48]>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:47][CH:48]=1)[NH:8][C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C:24]2=1

Komponenten

7

Edukt 5

HCID 702EthanolHCID 7967CyclohexanoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 9948495N-Benzhydrylidene-N'-(4-chlorophenyl)hydrazine

Produkt 1

HCID 3266156-Chloro-1,2,3,4-tetrahydrocarbazoleAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

N-(4-Chlorophenyl)benzophenone hydrazone (1.0 equiv., 0.5 mmol, 153 mg), cyclohexanone (1.5 equiv., 0.75 mmol, 0.078 mL), and TsOH.H2O (2 equiv., 1.0 mmol, 190 mg) were dissolved in ethanol (3 mL) and heated to reflux for 41 hours. The reaction mixture was then cooled to room temperature, diluted with Et2O (5 mL), neutralized with a saturated NaHCO3 solution, and extracted with Et2O (3×10 mL). The organic extracts were then dried over K2CO3, filtered and concentrated under vacuum. Purification by flash column chromatography (10% EtOAc/Hex) gave the title product as a white solid (94 mg, 0.46 mmol, 91% yield).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 41 hours
  3. extractionextracted with Et2O (3×10 mL)
  4. dry with materialThe organic extracts were then dried over K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by flash column chromatography (10% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-24ae813177714a139cfb504ee6595ac1
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235936B1

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