Dimethylformamide → 1,3,5-Tricarbethoxy-1,4-dihydro-2,6-dimethyl-4-(2-trifluoromethylphenyl)pyridine

HRID 1076267

Reaktionsgleichung

Reaktionsgleichung von HRID 1076267
[H-].[Na+].[C:3]([C:8]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])[C:12]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:11]([CH3:29])[NH:10][C:9]=1[CH3:30])([O:5][CH2:6][CH3:7])=[O:4].CN(C)C=[O:34].[O:36]1[CH2:40][CH2:39]C[CH2:37]1>C(#N)C>[C:37]([N:10]1[C:9]([CH3:30])=[C:8]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])[C:12]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:11]1[CH3:29])([O:36][CH2:40][CH3:39])=[O:34]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 1680891,4-Dihydro-2,6-dimethyl-4-(2-(trifluoromethyl)phenyl)-3,5-pyridinedicarboxylic acid diethyl ester

Produkt 1

HCID 121964581,3,5-Tricarbethoxy-1,4-dihydro-2,6-dimethyl-4-(2-trifluoromethylphenyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To 1.2 g. of sodium hydride (57% dispersion in mineral oil) suspended in tetrahydrofuran is added dropwise with stirring a solution of 10 g. of 3,5-dicarbethoxy-1,4-dihydro-2,6-dimethyl-4-(2-trifluoromethylphenyl)pyridine in tetrahydrofuran. The mixture is heated on a steam bath for 15 minutes, then it is cooled and enough dimethylformamide is added to dissolve the solid which has separated. To the resulting solution is added dropwise 3.04 g. of ethyl chloroformate and the reaction mixture is stirred at 25° for 15 minutes then heated on a steam bath for 12 hours. The mixture is filtered and concentrated to give an oil which is dissolved in acetonitrile. The solution is extracted with petroleum ether then concentrated to give an oil which is stirred with petroleum ether. The solid formed is filtered and the filtrate is concentrated in vacuo to give an oil which is chromatographed on an alumina "dry column" with methylene chloride as eluant to give 1,3,5-tricarbethoxy-1,4-dihydro-2,6-dimethyl-4-(2-trifluoromethylphenyl)pyridine, m.p. 56°-58°C.

Aufarbeitung

  1. additionis added dropwise
  2. temperatureThe mixture is heated on a steam bath for 15 minutes
  3. temperatureit is cooled
  4. dissolutionto dissolve the solid which
  5. customhas separated
  6. additionTo the resulting solution is added dropwise 3.04 g
  7. stirringof ethyl chloroformate and the reaction mixture is stirred at 25° for 15 minutes
  8. temperaturethen heated on a steam bath for 12 hours
  9. filtrationThe mixture is filtered
  10. concentrationconcentrated
  11. customto give an oil which
  12. extractionThe solution is extracted with petroleum ether
  13. concentrationthen concentrated
  14. customto give an oil which
  15. customThe solid formed
  16. filtrationis filtered
  17. concentrationthe filtrate is concentrated in vacuo
  18. customto give an oil which
  19. customis chromatographed on an alumina "
  20. dry with materialdry column" with methylene chloride as eluant

Quellen und Nachweise

ORD-Eintrag
ord-2bd16385e24446f3a227dd5827eb0e7a
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03956341

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