Citric Acid → Ethyl 2-benzyl-3-oxopropanoate

HRID 1445305

Reaktionsgleichung

Reaktionsgleichung von HRID 1445305
[H-].[Na+].[C:3]1([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:16](OCC)=[O:17].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH:16]([CH:10]([CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:17]

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 8025Ethyl formate2×HCID 16237Ethyl 3-phenylpropionateHCID 24758Sodium hydride2×

Produkt 1

HCID 562571Ethyl 2-benzyl-3-oxopropanoateAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension solution containing 4.4 g of 60% NaH in 200 ml of THF, 17.8 g of ethyl 3-phenylpropionate and 8.2 g of ethyl formate were added dropwise under ice cool for one hour. Thereafter, the mixture was stirred at room temperature for 15 hours. Furthermore, 14 g of 60 % NaH and 25.9 g of ethyl formate were divided into three parts and each part was added separately. Afterwards, the solution mixture was stirred at room temperature for 15 hours. After a 10% citric acid solution was added to the resultant reaction solution, the reaction solution was extracted with ethyl acetate and the extract was concentrated under reduced pressure to obtain 32.4 g of a brown oily concentrate. The concentrate thus obtained was purified by silica gel column chromatography to obtain 17.9 g of the titled compound as a transparent oily substance.

Aufarbeitung

  1. additionwere added dropwise under ice
  2. temperaturecool for one hour
  3. additioneach part was added separately
  4. stirringAfterwards, the solution mixture was stirred at room temperature for 15 hours
  5. customreaction solution
  6. extractionthe reaction solution was extracted with ethyl acetate
  7. concentrationthe extract was concentrated under reduced pressure
  8. customto obtain 32.4 g of a brown oily concentrate
  9. concentrationThe concentrate thus
  10. customobtained
  11. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-072297d6388b42499252a23ee3c7cb95
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666659B2

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