Potassium Iodide → Tert-butyl (1,2-diethyl-4-pyrazolidinylidene)acetate

HRID 2299111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299111
Cl[CH2:2][C:3]([CH2:12]Cl)=[CH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[CH2:22]([NH:24][NH:25][CH2:26][CH3:27])[CH3:23].[I-].[K+]>C(#N)C>[CH2:22]([N:24]1[CH2:12][C:3](=[CH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:2][N:25]1[CH2:26][CH3:27])[CH3:23]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 243721,2-Diethylhydrazine dihydrochlorideHCID 18379383Tert-butyl 4-chloro-3-(chloromethyl)-2-butenoate

Produkt 1

HCID 86584278Tert-butyl (1,2-diethyl-4-pyrazolidinylidene)acetateAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of tert-butyl 4-chloro-3-(chloromethyl)-2-butenoate (1.2 g, 5.3 mmol), potassium carbonate (4.0 g, 29 mmol), diethylhydrazine dihydrochloride (1.3 g, 8.0 mmol) and potassium iodide (0.86 g, 5.2 mmol) in acetonitrile was stirred at room temperature for 3 days. The mixture was filtered through celite, concentrated and purified by flash chromatography on silica gel eluting ethyl acetate:hexane (20:80, v;v) to give the tert-butyl (1,2-diethyl-4-pyrazolidinylidene)acetate (1.05 g, 82%) as an oil, MS (M+H)+=241.

Aufarbeitung

  1. filtrationThe mixture was filtered through celite,
  2. concentrationconcentrated
  3. custompurified by flash chromatography on silica gel
  4. washeluting ethyl acetate:hexane (20:80, v;v)

Quellen und Nachweise

ORD-Eintrag
ord-e3c9e8064684428cba98fb3a9db442bf
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495565B2

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