Isopropyl iodide → 5-(4-Benzyloxyphenyl)-2-isopropyl-2H-tetrazole

HRID 423255

Reaktionsgleichung

Reaktionsgleichung von HRID 423255
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[N:17][NH:18][N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:22](I)([CH3:24])[CH3:23]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]=[N:18][N:17]([CH:22]([CH3:24])[CH3:23])[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 47709095-[4-(benzyloxy)phenyl]-2H-tetrazole

Produkt 1

HCID 586297825-(4-Benzyloxyphenyl)-2-isopropyl-2H-tetrazoleAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-(4-Benzyloxyphenyl)-2H-tetrazole (500 mg) was added to a suspension of sodium hydride (96 mg) in dimethylformamide (5 mL) under ice-cooling. The mixture was stirred at room temperature for 0.5 hour. After addition of isopropyl iodide (405 mg) thereto, the mixture was stirred at 60° C. for 2 hours under heating. The reaction mixture was allowed to stand for cooling down to room temperature, diluted with ethyl acetate, washed with water and saturated brine, dried anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1, v/v) to give the title compound (571 mg).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at 60° C. for 2 hours
  3. temperatureunder heating
  4. temperaturefor cooling down to room temperature
  5. washwashed with water and saturated brine, dried anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane

Quellen und Nachweise

ORD-Eintrag
ord-f91d6be9cbca49738da14158e811620d
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101774B2

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