Diethyl Malonate → 2-(2,2,2-Trifluoro-1-phenylimino-ethyl)-malonic acid diethyl ester

HRID 1804884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804884
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[F:14][C:15]([F:26])([F:25])[C:16](Cl)=[N:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1.C(Cl)Cl>[CH2:12]([O:11][C:3](=[O:10])[CH:4]([C:16](=[N:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:15]([F:14])([F:25])[F:26])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:13]

Komponenten

6

Edukt 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 100588692,2,2-Trifluoro-N-phenylacetimidoyl Chloride

Produkt 1

HCID 572200902-(2,2,2-Trifluoro-1-phenylimino-ethyl)-malonic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of NaH (3.47 g, 145 mmol, 60% in mineral oil) in THF (200 mL) was added diethyl malonate (18.5 g, 116 mmol) at 0° C. The mixture was stirred for 30 min at this temperature and 2,2,2-trifluoro-N-phenyl-acetimidoyl chloride (19 g, 92 mmol) was added at 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was diluted with CH2Cl2, washed with saturated sodium bicarbonate solution and brine. The combined organic layers were dried over Na2SO4, filtered and concentrated to provide 2-(2,2,2-trifluoro-1-phenylimino-ethyl)-malonic acid diethyl ester, which was used directly in the next step without further purification.

Aufarbeitung

  1. additionwas added at 0° C
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-beada4b3452240c7a5b3069cc61a0de3
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354427B2

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