Ethyl formate → Ethyl 2-formyl-3-(5-pyrimidyl)propionate

HRID 967025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 967025
[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[N:3][CH:2]=1.[CH:14](OCC)=[O:15].[H-].[Na+]>C(COC)OC.C(OCC)(=O)C>[CH:14]([CH:8]([CH2:7][C:5]1[CH:6]=[N:1][CH:2]=[N:3][CH:4]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:15]

Komponenten

6

Edukt 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 21936199Ethyl 3-(5-pyrimidyl)propionate

Produkt 1

HCID 21936283Ethyl 2-formyl-3-(5-pyrimidyl)propionate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80711,2-DimethoxyethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Mixture of ethyl 3-(5-pyrimidyl)propionate (2.28 g) and ethyl formate (1.41 ml) dissolved in dry dimethoxyethane (5 ml) was added dropwise over 30 min to a suspension of sodium hydride (60%, 4.0 g) in DME (5 ml) under nitrogen, keeping the temperature below 0° C. Stirring was continued for a further 24 h, then the mixture was poured onto ice and washed with ether. The aqueous layer was adjusted to pH 7, then evaporated and the residue extracted with acetone. Filtration and evaporation gave crude product, which was taken up in ethyl acetate, charcoaled, dried and evaporated to give ethyl 2-formyl-3-(5-pyrimidyl)propionate. Like other compounds of this type, this proved difficult to characterise and was used without further purification.

Aufarbeitung

  1. customthe temperature below 0° C
  2. additionthe mixture was poured onto ice
  3. washwashed with ether
  4. customevaporated
  5. extractionthe residue extracted with acetone
  6. filtrationFiltration and evaporation
  7. customgave crude product, which
  8. customdried
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8ee170214dbf4de7b8a43251a5aeef55
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06953803B1

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