Methyl Ethyl Ketone → 2,3-Dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine-1-oxide

HRID 353003

Reaktionsgleichung

Reaktionsgleichung von HRID 353003
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][N+:3]=1[O-:12].C(C(C)=O)C.[F:18][C:19]([F:26])([C:22]([F:25])([F:24])[F:23])[CH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)P(=O)(N(C)C)N(C)C>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:21][CH2:20][C:19]([F:26])([F:18])[C:22]([F:25])([F:24])[F:23])[CH:5]=[CH:4][N+:3]=1[O-:12]

Komponenten

6

Edukt 4

HCID 6569Methyl Ethyl KetoneHCID 98722,2,3,3,3-PentafluoropropanolHCID 11430Potassium CarbonateHCID 1482232,3-Dimethyl-4-nitropyridine-N-oxide

Produkt 1

HCID 136547942,3-Dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine-1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12679HexamethylphosphoramideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 2,3-dimethyl-4-nitropyridine-1-oxide (2.0 g), methyl ethyl ketone (30 ml), 2,2,3,3,3-pentafluoropropanol (3.05 ml), anhydrous potassium carbonate (3.29 g) and hexamethylphosphoric acid triamide (2.07 g) was heated at 70-80° C. with stirring for 4.5 days. Then, the insoluble matter was filtered off and the filtrate was concentrated. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract layer was dried over magnesium sulfate, then the solvent was distilled off, and the residue was applied to a silica gel column (50 g). Elution with chloroform-methanol (10:1) and recrystallization from ethyl acetate-hexane gave 2.4 g of 2,3-dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine-1-oxide as colorless needles. Melting point 148-149° C.

Aufarbeitung

  1. filtrationThen, the insoluble matter was filtered off
  2. concentrationthe filtrate was concentrated
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract layer was dried over magnesium sulfate
  6. distillationthe solvent was distilled off
  7. washElution
  8. customwith chloroform-methanol (10:1) and recrystallization from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-cfd0985523954329ba0a8a210d647fb4
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06749864B2

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