Hydrochloric Acid → 4-(2,4-Bis-benzyloxy-5-bromo-phenyl)-2,4-dioxo-butyric acid ethyl ester

HRID 1891155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1891155
[Na].[CH2:2]([O:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([Br:24])=[CH:12][C:11]=1[C:25](=[O:27])[CH3:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:28](OCC)(=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30].Cl>C(O)C>[CH2:32]([O:31][C:29](=[O:30])[C:28](=[O:34])[CH2:26][C:25]([C:11]1[CH:12]=[C:13]([Br:24])[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][C:10]=1[O:9][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:27])[CH3:33]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 5360545SodiumHCID 247744411-(2,4-Bis-benzyloxy-5-bromo-phenyl)-ethanone

Produkt 1

HCID 592648154-(2,4-Bis-benzyloxy-5-bromo-phenyl)-2,4-dioxo-butyric acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

9.75 g sodium (0.424 mol, 3 eq) were dissolved in 500 ml absolute ethanol (1.5 hours). 58 g of 1-(2,4-Bis-benzyloxy-5-bromo-phenyl)-ethanone (0.141 mol, 1 eq) and 30.98 g diethyl oxalate (0.212 mol, 1.5 eq) were added and the mixture was refluxed for 2 hours. After cooling down, the mixture was poured onto 220 ml of 2N aqueous HCl and the product was extracted into 700 ml dichloromethane. The solvent was removed under reduced pressure and the yellow residue was triturated with 150 ml diethyl ether.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling down
  3. extractionthe product was extracted into 700 ml dichloromethane
  4. customThe solvent was removed under reduced pressure
  5. customthe yellow residue was triturated with 150 ml diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a2f2a2af2092419a978c7961f361f153
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507480B2

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