1,1,1-Trichloroethane → 4-Chlorophenyl-2-[2-(1,2,4-triazol-1-yl)-prop-2-yl]-oxirane

HRID 981539

Reaktionsgleichung

Reaktionsgleichung von HRID 981539
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]([CH3:16])([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH3:10])=[CH:4][CH:3]=1.[I-].[CH3:19][S+](C)(C)=O.[OH-].[Na+].CCCCCCCCCCCCCC[N+](C)(C)C.ClC(Cl)(Cl)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]([N:11]3[CH:15]=[N:14][CH:13]=[N:12]3)([CH3:10])[CH3:16])[CH2:19][O:17]2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 5

HCID 62781,1,1-TrichloroethaneHCID 14251TetradecyltrimethylammoniumHCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 133668554-Chlorophenyl 2-(1,2,4-triazol-1-yl)-prop-2-yl ketone

Produkt 1

HCID 133668634-Chlorophenyl-2-[2-(1,2,4-triazol-1-yl)-prop-2-yl]-oxiraneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4'-chloro-2-methyl-2-(1H-1,2,4-triazol-1-yl)propiophenone (1.375 g), trimethyl sulphoxonium iodide (1.6 g), aqueous sodium hydroxide (5N; 13.5 ml.), cetrimide (80 mg.) and 1,1,1-trichloroethane (30 ml.) was heated at 80° for 24 hours. The solution was cooled and diluted with methylene chloride (30 ml.), and the organic layer was separated and dried (MgSO4). Removal of the solvent, followed by flash chromatography of the residue on silica (100 g.) using ethyl acetate/hexane/diethylamine (40:60:3 v/v/v) for elution, gave, after collection of appropriate fractions and evaporation, the title oxirane as an oil in 79% yield, 1.15 g.

Aufarbeitung

  1. temperaturewas heated at 80° for 24 hours
  2. temperatureThe solution was cooled
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent
  6. washfor elution
  7. customgave
  8. customafter collection of appropriate fractions and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-d0ae63a853904f7ca0bc3f4b8bc88a2f
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04992454

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