Water → Ethyl 2-ethoxycarbonyl-3-(4-fluorobenzoyl)butanoate

HRID 1164815

Reaktionsgleichung

Reaktionsgleichung von HRID 1164815
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[CH:15]([CH3:25])[C:16]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[O:17].O>CN(C)C=O>[CH2:12]([O:11][C:3]([CH:4]([CH:15]([C:16](=[O:17])[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH3:25])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:10])[CH3:13]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 1449372-Chloro-1-(4-fluorophenyl)propan-1-one

Produkt 1

HCID 14293896Ethyl 2-ethoxycarbonyl-3-(4-fluorobenzoyl)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (50% oil dispersion, 3.5 g) was added with caution to a cooled solution of diethyl malonate (11.85 ml) in dimethylformamide (10 ml). The reaction mixture was stirred at room temperature for 30 minutes before a solution of 2-chloro-1-(4-fluorophenyl)-1-propanone (12.13 g) in dimethylformamide (50 ml) was added in small aliquots. The resulting reaction mixture was stirred for 2 hours at room temperature and then water (35 ml) was added. The mixture was extracted with petroleum ether (b.p. 40°-60° C.) (3×50 ml) and the combined organic extracts were evaporated under reduced pressure to afford ethyl 2-ethoxycarbonyl-3-(4-fluorobenzoyl)butanoate (15.92 g).

Aufarbeitung

  1. additionwas added in small aliquots
  2. customThe resulting reaction mixture
  3. extractionThe mixture was extracted with petroleum ether (b.p. 40°-60° C.) (3×50 ml)
  4. customthe combined organic extracts were evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a26f47df4f4e4d9994313c9e0e2d6b65
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04906628

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