Benzamide → Ethyl 2-benzoylamino-3-oxobutanoate

HRID 1799103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1799103
[N+:1](=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-].[C:12](N)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCCl.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Rh+3].[Rh+3]>[C:12]([NH:1][CH:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 2

HCID 2331BenzamideHCID 538206Ethyl diazoacetoacetate

Produkt 1

HCID 11425196Ethyl 2-benzoylamino-3-oxobutanoateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 86657289Di-rhodium tetraacetateKatalysatorHCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

A solution of ethyl 2-diazo-3-oxobutanoate (20 g, 128 mmol) in 1,2-dichloroethane (100 mL) was added over 16 h to a refluxing solution of benzamide (13 g, 107 mmol) and dirhodium tetraacetate (1.4 g, 3.2 mmol) in 1,2-dichloroethane (200 ml). The mixture was evaporated in vacuo and purified by flash chromatography to give ethyl 2-benzamido-3-oxobutanoate as a yellow oil (20 g, 50% yield).

Aufarbeitung

  1. customThe mixture was evaporated in vacuo
  2. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1878beb00ba04e64ace501885ea46426
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343997B2

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