Diisopropylamine → 4,5-Dichloro-2-methoxy-alpha-(2,3,4-trimethoxy-6-methylphenyl)-3-pyridinemethanol

HRID 242410

Reaktionsgleichung

Reaktionsgleichung von HRID 242410
C([Li])CCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([O:21][CH3:22])[CH:15]=1.ClC1C(Cl)=CN=C(OC)C=1[Li].[CH3:34][O:35][C:36]1[C:43]([O:44][CH3:45])=[C:42]([O:46][CH3:47])[CH:41]=[C:40]([CH3:48])[C:37]=1[CH:38]=[O:39]>O1CCCC1.O>[CH3:34][O:35][C:36]1[C:43]([O:44][CH3:45])=[C:42]([O:46][CH3:47])[CH:41]=[C:40]([CH3:48])[C:37]=1[CH:38]([C:15]1[C:16]([O:21][CH3:22])=[N:17][CH:18]=[C:19]([Cl:20])[C:14]=1[Cl:13])[OH:39]

Komponenten

8

Edukt 5

HCID 7912DiisopropylamineHCID 896832,3,4-Trimethoxy-6-methylbenzaldehydeHCID 230825824,5-Dichloro-2-methoxypyridineHCID 178418339ButyllithiumHCID 178506770HCID 178506770, Verbindung

Produkt 1

HCID 230826084,5-Dichloro-2-methoxy-alpha-(2,3,4-trimethoxy-6-methylphenyl)-3-pyridinemethanolAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

15.1 ml of n-butyllithium (1.57 mol/l hexane solution) was dropwise added at −20° C. to a solution having 2.40 g (23.7 mmol) of diisopropylamine dissolved in 30 ml of tetrahydrofuran, followed by stirring for 1 hour. The solution was cooled to −78° C., and a solution having 4.22 g (23.6 mmol) of 4,5-dichloro-2-methoxypyridine obtained in Step (e) dissolved in 20 ml of tetrahydrofuran was added, followed by stirring for 2 hours to prepare 4,5-dichloro-2-methoxy-3-pyridyllithium. Then, to this solution, a solution having 5.00 g (23.8 mmol) of 2,3,4-trimethoxy-6-methylbenzaldehyde dissolved in 20 ml of tetrahydrofuran was added, followed by stirring for 30 minutes. 50 ml of water was added to the mixture to terminate the reaction, and tetrahydrofuran was distilled off under reduced pressure. After extraction with ethyl ether, the organic layer was dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography to obtain 4.66 g (yield: 51%) of (2,3,4-trimethoxy-6-methylphenyl)(4,5-dichloro-2-methoxy-3-pyridyl)methanol.

Aufarbeitung

  1. additionwas added
  2. stirringby stirring for 2 hours
  3. additionwas added
  4. stirringby stirring for 30 minutes
  5. customto terminate
  6. customthe reaction, and tetrahydrofuran
  7. distillationwas distilled off under reduced pressure
  8. extractionAfter extraction with ethyl ether
  9. dry with materialthe organic layer was dried over sodium sulfate
  10. filtrationsubjected to filtration
  11. distillationthe solvent was distilled off under reduced pressure
  12. customfollowed by purification by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-350328760e4c4c22b3bf252a51fa5b41
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653113B2

Verknüpfte Notizen

Wird geladen…