Acetone → HCID 178467987, Verbindung

HRID 62371

Reaktionsgleichung

Reaktionsgleichung von HRID 62371
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([O:9]CC)=O)=[CH:3][CH:2]=1.[CH3:12][C:13]([CH3:15])=[O:14].C[O-].[Na+]>C1COCC1>[OH:14]/[C:13](/[CH3:15])=[CH:12]\[C:7]([C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)=[O:9]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 15291Ethyl isonicotinateHCID 10942334Sodium Methoxide

Produkt 1

HCID 178467987HCID 178467987, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-pyridinecarboxylate (30 g, 198 mmol) and acetone (34.58 g, 595 mmol) in THF (150 mL) was slowly added NaOMe (12.87 g, 238 mmol) at 35-40° C. The mixture was stirred at room temperature for 0.5 h, and then heated at reflux for 3 h. The mixture was cooled to room temperature and filtered to give a solid, which was washed with t-BuOMe, and dissolved in H2O. The solution was acidified with acetic acid and the resulting oily product was extracted with CHCl3. The solvent was removed in vacuo, and the crude product was obtained (12 g, 37%) and used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.73 (d, 2H), 7.76 (d, 2H), 6.63 (s, 1H), 2.21 (s, 3H); note: enolic OH does not appear.

Aufarbeitung

  1. customat 35-40° C
  2. temperatureheated
  3. temperatureat reflux for 3 h
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationfiltered
  6. customto give a solid, which
  7. washwas washed with t-BuOMe
  8. dissolutiondissolved in H2O
  9. extractionthe resulting oily product was extracted with CHCl3
  10. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2a25ccbc95514a82b066625d0e18f2e0
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446041B2

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