2-Acetylcyclopentanone → 2-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-3-methyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazole

HRID 1265180

Reaktionsgleichung

Reaktionsgleichung von HRID 1265180
[C:1]([CH:4]1[CH2:8][CH2:7][CH2:6][C:5]1=O)(=O)[CH3:2].[Cl:10][C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([Cl:21])[C:12]=1[NH:22][NH2:23]>CCO>[Cl:10][C:11]1[CH:16]=[C:15]([C:17]([F:19])([F:18])[F:20])[CH:14]=[C:13]([Cl:21])[C:12]=1[N:22]1[C:1]([CH3:2])=[C:4]2[CH2:8][CH2:7][CH2:6][C:5]2=[N:23]1

Komponenten

4

Edukt 2

HCID 984712-AcetylcyclopentanoneHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine

Produkt 1

HCID 186147432-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-3-methyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazoleAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Acetyl cyclopentanone (0.12 mL, 1 mmol) and 2,6-dichloro-4-trifluoromethylphenylhydrazine (245 mg, 1 mmol) in EtOH (10 mL) was heated under reflux for 12 hr. EtOH was removed under reduced pressure and the product purified by flash chromatography on silica (10% EtOAc:Hexane): yield 75%. 1H NMR (CDCl3) δ 7.8 (s, 2H), 2.6 (m, 6H each), 2.2 (s, 3H); MS (M+) 335.

Aufarbeitung

  1. temperatureunder reflux for 12 hr
  2. customEtOH was removed under reduced pressure
  3. customthe product purified by flash chromatography on silica (10% EtOAc:Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b8cd216525884c928aee59fbdc6f31bf
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06545033B1

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