Acetic Anhydride → HCID 23325041, Verbindung

HRID 1381002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1381002
[N:1]([O-])=O.[Na+].[C:5]([CH:11](C(C)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9].[C:20]([O:23]C(=O)C)(=O)[CH3:21]>O.C(O)(=O)C.[Zn]>[CH2:15]([O:14][C:12](=[O:13])[CH:11]([NH:1][C:20](=[O:23])[CH3:21])[C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9])[CH3:16]

Komponenten

7

Edukt 3

HCID 7918Acetic AnhydrideHCID 12688297HCID 12688297, VerbindungHCID 23668193Sodium Nitrite

Produkt 1

HCID 23325041HCID 23325041, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of sodium nitrite (41.3 g) in water was added slowly to a cooled solution of ethyl 2-valerylacetoacetate (118.7 g) in acetic acid (100 ml.), and the temperature was kept below 10°. Ice (100 g) was added, followed by acetic anhydride (105.0 g). Zinc dust (total 65.4 g) was added portionwise, keeping the temperature below 20° with stirring, until the reaction was complete. The mixture was allowed to stand overnight at room temperature, and it was then filtered. The solid was washed with chloroform, and the filtrate was extracted with chloroform. The chloroform extracts were washed with sodium carbonate solution and dried. The solvent was removed under vacuum, and the residue was purified by column chromatography (silica gel) eluting with petroleum ether (b.p. 60°-80°)/ethyl acetate, to yield ethyl-2-acetamido-3-oxoheptanoate, 13.5 g, which was used without further purification.

Aufarbeitung

  1. customwas kept below 10°
  2. customthe temperature below 20°
  3. filtrationit was then filtered
  4. washThe solid was washed with chloroform
  5. extractionthe filtrate was extracted with chloroform
  6. washThe chloroform extracts were washed with sodium carbonate solution
  7. customdried
  8. customThe solvent was removed under vacuum
  9. customthe residue was purified by column chromatography (silica gel)
  10. washeluting with petroleum ether (b.p. 60°-80°)/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-70b5844e7fd44e40adfdb238f6f65137
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04584384

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