Diethyl Malonate → HCID 22718000, Verbindung

HRID 1582593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582593
[O-]CC.[Na+].[C:5]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30]Br)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]([O:13][CH2:14][CH3:15])=[O:12])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 22714477Benzyl (4-bromobutyl)carbamate

Produkt 1

HCID 22718000HCID 22718000, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

An ethanol (130.2 ml) solution of sodium ethoxide (5.83 g) was added with diethyl malonate (13 ml) and stirred at room temperature for 5 minutes. This solution was added with an ethanol (55.8 ml) solution of the 1-benzyloxycarbonylamino-4-bromobutane (4.9 g) obtained in the above step (b), and stirred at 40° C. for 20 hours. The reaction system was concentrated under reduced pressure without any treatment, and the residue was added with saturated aqueous ammonium chloride, and then the organic substances were extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (1.2 kg, hexane:ethyl acetate=2:1) to obtain diethyl 2-(4-benzyloxycarbonylaminobutyl)malonate (5.2 g, 83%).

Aufarbeitung

  1. customobtained in the above step (b)
  2. stirringstirred at 40° C. for 20 hours
  3. concentrationThe reaction system was concentrated under reduced pressure without any treatment
  4. additionthe residue was added with saturated aqueous ammonium chloride
  5. extractionthe organic substances were extracted with ethyl acetate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (1.2 kg, hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-e087ff0853d645918bc8eb8fc5a0a963
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06737416B2

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