Potassium Iodide → 1-[2-(4-{2-[2-(4-Difluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]triazole

HRID 2113887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2113887
[CH3:1][C:2]1[CH:3]=[C:4]([OH:17])[CH:5]=[CH:6][C:7]=1[CH2:8][O:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[N:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:25][C:26]1[N:27]=[C:28]([CH:31]=[CH:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH:40]([F:42])[F:41])=[CH:35][CH:34]=2)[O:29][CH:30]=1.[I-].[K+]>CC(=O)CC>[F:42][CH:40]([F:41])[O:39][C:36]1[CH:37]=[CH:38][C:33]([CH:32]=[CH:31][C:28]2[O:29][CH:30]=[C:26]([CH2:25][O:17][C:4]3[CH:5]=[CH:6][C:7]([CH2:8][O:9][CH2:10][CH2:11][N:12]4[CH:16]=[CH:15][N:14]=[N:13]4)=[C:2]([CH3:1])[CH:3]=3)[N:27]=2)=[CH:34][CH:35]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 691125744-(Chloromethyl)-2-{2-[4-(difluoromethoxy)phenyl]ethenyl}-1,3-oxazoleHCID 692910153-Methyl-4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenol

Produkt 1

HCID 692923021-[2-(4-{2-[2-(4-Difluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]triazoleAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 201 mg (0.86 mmol) 3-methyl-4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenol and 169 mg (0.52 mmol) cesium carbonate in 10 ml 2-butanone was stirred at 60° C. for 30 minutes, then 246 mg (0.86 mmol) 4-chloromethyl-2-[2-(4-difluoromethoxy-phenyl)-vinyl]-oxazole and 143 mg (0.86 mmol) potassium iodide were added and stirring was continued overnight. After evaporation, the residue was mixed with aqueous NaOH (1N) and extracted with ethyl acetate. The combined extracts were dried, evaporated and the product purified on silica (ethyl acetate) to yield 242 mg (59%) 1-[2-(4-{2-[2-(4-Difluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]triazole as a white solid melting at 119-120° C.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued overnight
  3. customAfter evaporation
  4. additionthe residue was mixed with aqueous NaOH (1N)
  5. extractionextracted with ethyl acetate
  6. customThe combined extracts were dried
  7. customevaporated
  8. customthe product purified on silica (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-012e593257834491b8ef65f02f9e5a91
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07432291B2

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