Dimethylformamide → Ethyl 2-(2-benzoyloxyethoxyimino)-3-oxobutyrate

HRID 1154111

Reaktionsgleichung

Reaktionsgleichung von HRID 1154111
[OH:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:12]([O:20][CH2:21][CH2:22]Br)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[C:12]([O:20][CH2:21][CH2:22][O:1][N:2]=[C: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

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5230902-Bromoethyl BenzoateHCID 178472877HCID 178472877, Verbindung

Produkt 1

HCID 53765835Ethyl 2-(2-benzoyloxyethoxyimino)-3-oxobutyrateAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 15.7 g.), 2-bromoethyl benzoate (27.5 g.), potassium carbonate (20.7 g.), N,N-dimethylformamide (25 ml.) and ethyl acetate (25 ml.) was stirred at room temperature for 4 hrs. The reaction mixture was treated in a conventional manner to give ethyl 2-(2-benzoyloxyethoxyimino)-3-oxobutyrate (syn isomer, 28 g.). (2) A solution of ethyl 2-(2-benzoyloxyethoxyimino)-3-oxobutyrate (syn isomer, 28 g.), sulfuryl chloride (13.5 g.) and acetic acid (30 ml.) was stirred at 40° C. for 10 minutes and at room temperature for 5.5 hrs. The reaction mixture was treated in a conventional manner to give ethyl 2-(2-benzoyloxyethoxyimino)-4-chloro-3-oxobutyrate (syn isomer, 29 g.).

Aufarbeitung

  1. additionThe reaction mixture was treated in a conventional manner

Quellen und Nachweise

ORD-Eintrag
ord-b1dc8f0ad8da4a989d8c393cd6b3d625
Quelldatensatz
uspto-grants-1984_12
Patentnummer
US04487767

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