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Iodine → HCID 19789782, Verbindung

HRID 1655938
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1655938
[CH2:1](Br)[CH:2]=[CH2:3].[Cl:5][C:6]1([C:9](=[O:16])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH2:8][CH2:7]1.II>O1CCCC1.[Zn]>[Cl:5][C:6]1([C:9]([OH:16])([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH2:3][CH:2]=[CH2:1])[CH2:8][CH2:7]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 807IodineHCID 7841Allyl bromideHCID 143483801-(1-Chlorocyclopropyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one

Produkt 1

HCID 19789782HCID 19789782, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

A solution of 12. 1 g (0.1 mol) of allyl bromide and 16.65 g (0.09 mol) of 1-(1-chlorocyclopropyl)-2-(1,2,4-triazol-1-yl)-ethan-1-one in 50 ml of tetrahydrofuran are added dropwise at 20° C. under nitrogen atmosphere in the course of 0.5 hours to a stirred mixture of 7.2 g (0.11 mol) of zinc dust, 0.1 g of iodine and 50 ml of absolute tetrahydrofuran. When the addition has ended, stirring is continued for 24 hours at room temperature, the mixture is then concentrated by stripping off the solvent and treated with aqueous ammonium chloride solution. The resulting mixture is extracted several times using dichloromethane. The combined organic phases are dried over sodium sulphate and then concentrated by stripping off the solvent under reduced pressure. In this manner, 10.2 g (50% of theory) of (4-(1-chloro-cyclopropyl)-4-hydroxy-5-(1,2,4-triazol1-yl)-pent-1-ene are obtained in the form of a solid substance of melting point 75° to 76° C. ##STR40##

Aufarbeitung

  1. additionWhen the addition
  2. concentrationthe mixture is then concentrated
  3. additiontreated with aqueous ammonium chloride solution
  4. extractionThe resulting mixture is extracted several times
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3ecdc55feb314ae58abfc300035deed0
Quelldatensatz
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05252582

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