Acetic Acid → 3-[3-Chloro-5-(trifluoromethyl)-2-pyridyl]-1-(2-nitrophenyl)-2-propen-1-one

HRID 495394

Reaktionsgleichung

Reaktionsgleichung von HRID 495394
[OH-].[Na+].[N+:3]([CH2:6][C:7]([C:9]1C=CC=[CH:11][CH:10]=1)=O)([O-:5])=[O:4].[Cl:15][C:16]1[C:17]([CH:26]=O)=[N:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1.[C:28]([OH:31])(=O)[CH3:29].[CH2:32](O)C>O>[Cl:15][C:16]1[C:17]([CH:26]=[CH:32][C:28]([C:29]2[CH:11]=[CH:10][CH:9]=[CH:7][C:6]=2[N+:3]([O-:5])=[O:4])=[O:31])=[N:18][CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 948332-Nitro-1-phenylethanoneHCID 220187903-Chloro-5-(trifluoromethyl)picolinaldehyde

Produkt 1

HCID 686164013-[3-Chloro-5-(trifluoromethyl)-2-pyridyl]-1-(2-nitrophenyl)-2-propen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium hydroxide (0.55 g) was dissolved in water (5 ml) and the resulting solution was diluted with ethanol (3 ml). 2-Nitroacetophenone (1.8 g) was added at 20° C., and the solution was stirred for 5 minutes. 3-Chloro-5-(trifluoromethyl)pyridine-2-carboxaldehyde (2.25 g) was added and stirring was continued for 16 hours. The solution was acidified with acetic acid, the organic layer separated, dried over magnesium sulfate, filtered and evaporated to give a brown oil. Silica gel column chromatography, followed by recrystallisation (petrol) afforded the title compound, 88-9° C.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 16 hours
  3. customthe organic layer separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a brown oil
  8. customSilica gel column chromatography, followed by recrystallisation (petrol)

Quellen und Nachweise

ORD-Eintrag
ord-3939677ceb034ef6ba89aa773beedaf9
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06939882B1

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