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Diisopropylamine → (2,3,4-Trimethoxy-6-methylphenyl)(2-fluoro-4-iodo-5-methyl-3-pyridyl)methanol

HRID 242413
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 242413
C(NC(C)C)(C)C.FC1C(I)=CC(C)=CN=1.FC1C(I)=C([Li])C(C)=CN=1.[F:27][C:28]1[C:33]([Li])=[C:32]([I:35])[C:31]([CH3:36])=[CH:30][N:29]=1.[CH3:37][O:38][C:39]1[C:46]([O:47][CH3:48])=[C:45]([O:49][CH3:50])[CH:44]=[C:43]([CH3:51])[C:40]=1[CH:41]=[O:42]>O1CCCC1.O.CCCCCC>[CH3:37][O:38][C:39]1[C:46]([O:47][CH3:48])=[C:45]([O:49][CH3:50])[CH:44]=[C:43]([CH3:51])[C:40]=1[CH:41]([C:33]1[C:28]([F:27])=[N:29][CH:30]=[C:31]([CH3:36])[C:32]=1[I:35])[OH:42]
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Komponenten

9

Edukt 5

HCID 7912DiisopropylamineHCID 896832,3,4-Trimethoxy-6-methylbenzaldehydeHCID 102432202-Fluoro-3-iodo-5-methylpyridineHCID 178506733HCID 178506733, VerbindungHCID 178506759HCID 178506759, Verbindung

Produkt 1

HCID 23082609
(2,3,4-Trimethoxy-6-methylphenyl)(2-fluoro-4-iodo-5-methyl-3-pyridyl)methanol
Ausbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

8.90 ml (1.57 mol/l hexane solution) was dropwise added at −78° C. to a solution having 1.34 g (13.3 mmol) of diisopropylamine dissolved in 27 ml of tetrahydrofuran, followed by stirring for 30 minutes. To this solution, a solution having 3.15 g (13.3 mmol) of 2-fluoro-3-iodo-5-methylpyridine obtained in Step (a) dissolved in 5 ml of tetrahydrofuran was added, followed by stirring for 1 hour, so that 2-fluoro-3-iodo-5-methyl-4-pyridyllithium formed at the initial stage was isomerized to 2-fluoro-4-iodo-5-methyl-3-pyridyllithium. To the reaction mixture, a solution having 2.79 g (13.3 mmol) of 2,3,4-trimethoxy-6-methylbenzaldehyde dissolved in 5 ml of tetrahydrofuran was added, followed by stirring for 2 hours. After the temperature was increased to room temperature, 50 ml of water was added, followed by extraction with ethyl ether. The organic layer was dried over magnesium sulfate and subjected to filtration, the solvent was distilled off under reduced pressure, and the obtained crude product was purified by silica gel chromatography to obtain 4.45 g (yield: 75%) of (2,3,4-trimethoxy-6-methylphenyl)(2-fluoro-4-iodo-5-methyl-3-pyridyl)methanol.

Aufarbeitung

  1. additionwas added
  2. customformed at the initial stage
  3. additionwas added
  4. stirringby stirring for 2 hours
  5. extractionfollowed by extraction with ethyl ether
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationsubjected to filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe obtained crude product
  10. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4b62ab959cb94808b36439649d99279d
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08653113B2

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