Tetrahydrofuran → (E)-3-[4-(4-Fluorophenyl)-6-isopropyl-2-methoxy-3-methoxymethyl-pyridin-5-yl]-prop-2-enal

HRID 36918

Reaktionsgleichung

Reaktionsgleichung von HRID 36918
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](C=O)=[C:14]([CH:18]([CH3:20])[CH3:19])[N:13]=[C:12]([O:21][CH3:22])[C:11]=2[CH2:23][O:24][CH3:25])=[CH:6][CH:5]=1.O.O.C(O)(=O)C(O)=O.[O:34]1C[CH2:37][CH2:36][CH2:35]1>O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](/[CH:37]=[CH:36]/[CH:35]=[O:34])=[C:14]([CH:18]([CH3:20])[CH3:19])[N:13]=[C:12]([O:21][CH3:22])[C:11]=2[CH2:23][O:24][CH3:25])=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 61373Oxalic acid dihydrateHCID 199366934-(4-Fluorophenyl)-6-isopropyl-2-methoxy-3-methoxymethyl-pyridine-5-carbaldehyde

Produkt 1

HCID 19936689(E)-3-[4-(4-Fluorophenyl)-6-isopropyl-2-methoxy-3-methoxymethyl-pyridin-5-yl]-prop-2-enal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

804 (3.1 mmol) of diethyl 2-(cyclohexylamino)-vinyl-phosphate dissolved in 6 ml of dry tetrahydrofuran are added dropwise under nitrogen to a suspension of 59 mg (2.5 mmol) of sodium hydride in 6 ml of dry tetrahydrofuran at -5° C. After 30 min, 0.65 g (2.05 mmol) of the compound from Example 9 in 15 ml of dry tetrahydrofuran is added dropwise at the same temperature and the mixture is heated to reflux for 30 min. After cooling to room temperature, the mixture is added to 200 ml of ice-cold water and extracted three times using 100 ml of ethyl acetate each time. The combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulphate. After concentration in vacuo, the residue is taken up in 5 ml of toluene, treated with a solution of 0.9 g (7 mmol) of oxalic acid dihydrate in 12 ml of water and heated to reflux for 90 min. After cooling to room temperature, the phases are separated, and the organic phase is washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated in vacuo. The residue is dissolved in methylene chloride and filtered through silica gel.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 30 min
  3. extractionextracted three times
  4. washThe combined organic phases are washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationAfter concentration in vacuo
  7. temperatureheated
  8. temperatureto reflux for 90 min
  9. temperatureAfter cooling to room temperature
  10. customthe phases are separated
  11. washthe organic phase is washed with saturated sodium chloride solution
  12. dry with materialdried over sodium sulphate
  13. concentrationconcentrated in vacuo
  14. dissolutionThe residue is dissolved in methylene chloride
  15. filtrationfiltered through silica gel

Quellen und Nachweise

ORD-Eintrag
ord-71320257f16b4873a998fad0d7a02c00
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418243

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