Water → HCID 10946371, Verbindung

HRID 1647954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647954
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]2([C:10]3([F:13])[CH2:12][CH2:11]3)[CH2:9][O:8]2)=[CH:4][CH:3]=1.[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1.O>CN(C)C=O>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]([C:10]2([F:13])[CH2:12][CH2:11]2)([OH:8])[CH2:9][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 22400786HCID 22400786, Verbindung

Produkt 1

HCID 10946371HCID 10946371, VerbindungAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 3.3 g (15.7 mmol) of 2-(4-chlorobenzyl)-2-(1-fluorocyclopropyl)-oxirane in 10 ml of dimethylformamide is added dropwise to a mixture of 3.3 g (47.1 mmol) of 1,2,4-triazole end 0.35 g (3.14 mmol) of potassium tert.-butylate in 20 ml of dimethylformamide at a temperature of 80° C., while stirring. When the addition has ended, the reaction mixture is stirred for 13 hours at 80° C. The solvent is then stripped off under reduced pressure, and the remaining residue is taken up with water. The aqueous phase is extracted four times with methylene chloride. The combined organic phases are dried over sodium sulphate and then concentrated under reduced pressure. The remaining residue is chromatographed over silica over silica gel using cyclohxane:ethylacetate=2:1 as the mobile phase. Evaporation of the eluate gives 2.2 g (47% of theory) of 1-(4-chlorophenyl)-2-(1-fluorocyclopropyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol in form of a solid substance.

Aufarbeitung

  1. additionWhen the addition
  2. stirringthe reaction mixture is stirred for 13 hours at 80° C
  3. extractionThe aqueous phase is extracted four times with methylene chloride
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe remaining residue is chromatographed over silica over silica gel using cyclohxane
  7. customEvaporation of the eluate

Quellen und Nachweise

ORD-Eintrag
ord-0994ba4deb4d4d23be0683ee22413642
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05434303

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