Methyl butadienecarboxylate → HCID 20435989, Verbindung

HRID 1154033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1154033
[CH3:1][C:2]1([CH2:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[C:6](=[O:7])[NH:5][NH:4][C:3]1=[O:8].ClOC(C)(C)C.[C:24]([O:30][CH3:31])(=[O:29])[CH:25]=[CH:26][CH:27]=[CH2:28]>O1CCOCC1>[CH3:1][C:2]1([CH2:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[C:6](=[O:7])[N:5]2[CH2:28][CH:27]=[CH:26][CH:25]([C:24]([O:30][CH3:31])=[O:29])[N:4]2[C:3]1=[O:8]

Komponenten

5

Edukt 3

HCID 73688Methyl butadienecarboxylateHCID 521297Tert-Butyl hypochloriteHCID 20435928HCID 20435928, Verbindung

Produkt 1

HCID 20435989HCID 20435989, VerbindungAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel3×

Versuchsvorschrift

(B)(a) 1.21 g (5 mmol) of 4-methyl-4-[2-(tetrahydro-2-pyranyloxy)ethyl]pyrazolidine-3,5-dione were suspended in 20 ml of dry dioxan and the suspension was stirred at room temperature under a stream of nitrogen. A solution of 0.543 g (5 mmol) of tert.butyl hypochlorite in 5 ml of dry dioxan was added over a period of 15 minutes. The resulting blue solution was filtered and the filtrate was evaporated in vacuo. The residue was dissolved in 10 ml of dry dioxan and the solution was added portionwise to a stirred solution of 0.616 g (5.5 mmol) of methyl penta-2,4-dienoate in 20 ml of dry dioxan. The blue color was allowed to fade between additions. When the addition was complete and no blue color persisted, the solution was stirred at room temperature for 1 hour. The resulting solution was evaporated in vacuo and the residue was chromatographed on silica gel. Elution with diethyl ether gave 0.52 g (29%) of methyl 2,3,5,8-tetrahydro-2-methyl-1,3-dioxo-2-[2-(tetrahydro-2-pyranyloxy)ethyl]-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate having a melting point of 127.5°-128.5° C. (from diethyl ether).

Aufarbeitung

  1. filtrationThe resulting blue solution was filtered
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in 10 ml of dry dioxan
  4. additionWhen the addition
  5. stirringthe solution was stirred at room temperature for 1 hour
  6. customThe resulting solution was evaporated in vacuo
  7. customthe residue was chromatographed on silica gel
  8. washElution with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-aecf0ead38d44e3ca140c690b1352bb6
Quelldatensatz
uspto-grants-1984_12
Patentnummer
US04487929

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