Sodium hydride → 2-(2,5Difluoro-phenyl)-cyclopropanecarboxylic acid methoxy-methyl-amide

HRID 857017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857017
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[CH:17]=[CH:18][C:19]([N:21]([O:23][CH3:24])[CH3:22])=[O:20]>CN(C=O)C>[CH3:24][O:23][N:21]([CH3:22])[C:19]([CH:18]1[CH2:4][CH:17]1[C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[F:9])=[O:20]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 738515783-(2,5-difluoro-phenyl)-N-methoxy-N-methyl-acrylamide

Produkt 1

HCID 587594682-(2,5Difluoro-phenyl)-cyclopropanecarboxylic acid methoxy-methyl-amideAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (8 g, 60% oil dispersion) was added to a suspension of trimethylsulfoxonium iodide (44 g) in DMF (150 mL) at 0° C. The resulting mixture was allowed to warm to room temperature and stirred for 0.5 h. A solution of 3-(2,5-difluoro-phenyl)-N-methoxy-N-methyl-acrylamide (21 g) was added to the above reaction mixture at 0° C., and the resulting reaction was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with water and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo to give a residue. The residue was purified by flash chromatography over silica gel (elution with 50% hexanes in ethyl acetate) to give the title compound (18 g) as an oil.

Aufarbeitung

  1. customthe resulting reaction
  2. temperatureto warm to room temperature
  3. stirringstirred for 2 h
  4. customThe reaction was quenched with water
  5. extractionthe aqueous layer was extracted with CH2Cl2
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto give a residue
  10. customThe residue was purified by flash chromatography over silica gel (elution with 50% hexanes in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-176278b2eeea4c12925d5df120b4f7fc
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144881B2

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