Trifluoroacetonitrile → Methyl 1,6-dihydro-4-hydroxy-6-oxo-2-(trifluoromethyl)-3-pyridinecarboxylate

HRID 251573

Reaktionsgleichung

Reaktionsgleichung von HRID 251573
CO[C:3]([CH2:5][C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:7])=[O:4].CC(C)([O-])C.[K+].[F:19][C:20]([F:24])([F:23])[C:21]#[N:22]>C1COCC1>[CH3:12][O:11][C:9]([C:8]1[C:6]([OH:7])=[CH:5][C:3](=[O:4])[NH:22][C:21]=1[C:20]([F:24])([F:23])[F:19])=[O:10]

Komponenten

5

Edukt 3

HCID 67710TrifluoroacetonitrileHCID 74591Dimethyl 3-oxoglutarateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 54717819Methyl 1,6-dihydro-4-hydroxy-6-oxo-2-(trifluoromethyl)-3-pyridinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Dimethyl 1,3-acetonedicarboxylate (34.8 g, 0.2 mol) is slowly added to a solution of potassium t-butoxide (22.4 g, 0.2 mol) in THF (300 mL) at 60° C. After addition, the reaction mixture is stirred at 60° C. for 2 hours. The reaction is allowed to cool to 40° C. and trifluoroacetonitrile gas (100 g, 1.05 mol) is slowly bubbled slowly into the above mixture. The reaction temperature is maintained at 50° C. overnight. The volatile material is removed in vacuo. The residue is dissolved in water (200 mL) and the solution is poured into hydrogen chloride solution (conc. HCl/water 80 mL: 200 mL). The white solid is collected by filtration and dried. After being triturated with chloroform (200 mL), the title product is obtained as a white solid. 1H NMR: (CDCl3) 6.29 (s, 1H), 3.76 (s, 3H).

Aufarbeitung

  1. additionAfter addition
  2. temperatureto cool to 40° C.
  3. temperatureThe reaction temperature is maintained at 50° C. overnight
  4. customThe volatile material is removed in vacuo
  5. dissolutionThe residue is dissolved in water (200 mL)
  6. additionthe solution is poured into hydrogen chloride solution (conc. HCl/water 80 mL: 200 mL)
  7. filtrationThe white solid is collected by filtration
  8. customdried
  9. customAfter being triturated with chloroform (200 mL)

Quellen und Nachweise

ORD-Eintrag
ord-a7c53e11eb8044b49cde5ec5c7a588d7
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863454B2

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