Ammonium Chloride → CID 275522

HRID 62389

Reaktionsgleichung

Reaktionsgleichung von HRID 62389
[O:1]=[C:2]([CH2:8][C:9](=[O:11])[CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(OCC)(OCC)O[CH2:14][CH3:15].[Cl-].[NH4+]>C(O)C>[CH2:14]([O:11][C:9]([CH3:10])=[CH:8][C:2](=[O:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:15]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 31214Ethyl orthoformateHCID 69208Ethyl 2,4-dioxovalerate

Produkt 1

HCID 275522CID 275522Ausbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 2,4-dioxopentanoate (36.5 g, 231 mmol) and triethyl orthoformate (41 mL, 246 mmol) in ethanol (60 mL) was added ammonium chloride (3.7 g, 69 mmol). The suspension was stirred at RT overnight. LCMS showed that the reaction was mostly complete. (Hydrolyzes on LCMS to some degree?) The reaction was concentrated under vacuum. The remaining oil was taken up in Et2O (300 mL), filtered to remove insolubles, rinsed with Et2O, and concentrated under vacuum. The product was obtained by short path distillation under vacuum (bp 70 to 77° C. at 0.09 mmHg) to give the product ethyl 4-ethoxy-2-oxopent-3-enoate (36.5 g, 47.3 mmol, 79% yield) as a light yellow oil.

Aufarbeitung

  1. concentration) The reaction was concentrated under vacuum
  2. filtrationfiltered
  3. customto remove insolubles
  4. washrinsed with Et2O
  5. concentrationconcentrated under vacuum
  6. customThe product was obtained by short path distillation under vacuum (bp 70 to 77° C. at 0.09 mmHg)

Quellen und Nachweise

ORD-Eintrag
ord-eeb4172da1ee4a41bf96dbfbbdd0ffdc
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446041B2

Verknüpfte Notizen

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