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Methyl iodide → 1-(4-Chlorophenyl)-4,4-dimethyl-3-methoxy-2-(1,2,4-triazole-1-yl)-1-pentene

HRID 1583710
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1583710
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:10]([OH:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23]I>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:10]([O:15][CH3:23])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 917371-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-pentene-3-ol

Produkt 1

HCID 541861491-(4-Chlorophenyl)-4,4-dimethyl-3-methoxy-2-(1,2,4-triazole-1-yl)-1-penteneAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Versuchsvorschrift

The I'-B isomer (2 g) of 1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-pentene-3-ol (Compound No. 1) was dissolved in dimethylformamide (20 cc), and 65% sodium hydride (0.26 g) was added thereto. After stirring at room temperature for 1 hour, the reaction mixture was cooled to 10° C., and methyl iodide (1 g) was added. The reaction mixture was kept at 10° C. for 1 hour and then allowed to stand at room temperature for 16 hours. Dimethylformamide was removed under reduced pressure, and the residue was extracted with addition of ice water (100 g) and chloroform (100 cc). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting crude product was purified by column chromatography on silica gel (acetone:n-hexane=1:10) to obtain 1.0 g of the entitled compound as an oily product.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to 10° C.
  2. waitThe reaction mixture was kept at 10° C. for 1 hour
  3. waitto stand at room temperature for 16 hours
  4. customDimethylformamide was removed under reduced pressure
  5. extractionthe residue was extracted with addition of ice water (100 g) and chloroform (100 cc)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe resulting crude product was purified by column chromatography on silica gel (acetone:n-hexane=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-f8265ba329084370b4324cf719289912
Quelldatensatz
uspto-grants-1985_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04554007

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