Potassium Carbonate → 1-Phenyl-5-(5-trifluoromethyl-thiophen-3-yloxy)-1H-tetrazole

HRID 6973

Reaktionsgleichung

Reaktionsgleichung von HRID 6973
[F:1][C:2]([F:10])([F:9])[C:3]1[S:7][CH:6]=[C:5]([OH:8])[CH:4]=1.Cl[C:12]1[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:15]=[N:14][N:13]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:17]1([N:16]2[C:12]([O:8][C:5]3[CH:4]=[C:3]([C:2]([F:10])([F:9])[F:1])[S:7][CH:6]=3)=[N:13][N:14]=[N:15]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 110842734-Hydroxy-2-(trifluoromethyl)thiophene

Produkt 1

HCID 220194661-Phenyl-5-(5-trifluoromethyl-thiophen-3-yloxy)-1H-tetrazoleAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 5-trifluoromethyl-thiophen-3-ol (2.0 g, 11.9 mmol) in dry acetone (480 mL) containing 5-chloro-1-phenyl-1H-tetrazole (2.1 g, 11.9 mmol) and K2CO3 (3.3 g, 23.8 mmol) is maintained at reflux with careful exclusion of moisture overnight. The acetone is removed under reduced pressure and the residue is partitioned between CH2Cl2 (500 mL) and H2O (50 mL). The organic extracts are washed with brine, then dried (Na2SO4), filtered and concentrated. The crude product is chromatographed on silica gel, eluting with EtOAc:Hex (1:80) to afford the title compound (2.5 g, 68%) as a white solid.

Aufarbeitung

  1. temperatureis maintained
  2. temperatureat reflux with careful exclusion of moisture overnight
  3. customThe acetone is removed under reduced pressure
  4. customthe residue is partitioned between CH2Cl2 (500 mL) and H2O (50 mL)
  5. washThe organic extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is chromatographed on silica gel
  10. washeluting with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-97bd380cae1c4e708eb824535de2f9eb
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084170B2

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