Reaktion #544539

ord-f1ea22a361764df3b5d710881fffcea4

Reaktionsgleichung

CCOC(=O)C(=O)OCC
Diethyl oxalate
CC[O-].[Na+]
sodium ethoxide
CCCCCC(=O)c1ccccc1
Hexanophenone
→
CCCCC(C(=O)C(=O)OCC)C(=O)c1ccccc1
product ( 172 )
CCCCC(C(=O)C(=O)OCC)C(=O)c1ccccc1
3-Benzoyl-2-oxo-heptanoic acid ethyl ester

Edukte

CCOC(=O)C(=O)OCC
Diethyl oxalate
CC[O-].[Na+]
sodium ethoxide
CCCCCC(=O)c1ccccc1
Hexanophenone

Reagenzien

Keine

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenAfter concentration the residue
  2. 2
    Sonstigeis partitioned between 3N HCl and ethyl acetate
  3. 3
    Extraktionextracted with ethyl acetate
  4. 4
    WaschenCombined organic layers are washed with brine
  5. 5
    Trocknendried with anhydrous Na2SO4
  6. 6
    SonstigePurification by column chromatography with hexane/ethyl acetate

Vorschrift

Diethyl oxalate (7.31 g, 0.05 mol) is added to freshly made sodium ethoxide (1.05 eq.) in ethanol. Hexanophenone (8.81 g, 0.05 mol) is added dropwise, and the resulting mixture is stirred at room temperature overnight. After concentration the residue is partitioned between 3N HCl and ethyl acetate, extracted with ethyl acetate. Combined organic layers are washed with brine and dried with anhydrous Na2SO4. Purification by column chromatography with hexane/ethyl acetate gives the product (172).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07186734B2uspto-grants-2007_03