Water → 1-[2-(4-nitro-benzyloxy)-ethyl]-1H-[1,2,3]triazole

HRID 1271423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271423
[N:1]1([CH2:6][CH2:7][OH:8])[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].I[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.O>C1COCC1.C(OCC)(=O)C>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][O:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)=[CH:14][CH:15]=1)([O-:21])=[O:20]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 76598alpha-Iodo-p-nitrotolueneHCID 99892372-(1H-1,2,3-triazol-1-yl)ethan-1-ol

Produkt 1

HCID 184535171-[2-(4-nitro-benzyloxy)-ethyl]-1H-[1,2,3]triazoleAusbeute 27,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-[1,2,3]triazol-1-yl-ethanol (5.98 g, 52.84 mmol) in dry THF (150 ml) at −50° C. sodium hydride (1.27 g, 52.84 mmol) was added and the mixture stirred for 45 min. followed by the addition of 1-iodomethyl-4-nitro-benzene (13.9 g, 52.84 mmol). The mixture was refluxed for 2 h, water (100 ml) and ethyl acetate (150 ml) were added and the resulting precipitate removed by filtration. The filtrate was concentrated and the residue purified by flash column chromatography (ethyl acetate 100%) yielding 3.6 g (27%) 1-[2-(4-nitro-benzyloxy)-ethyl]-1H-[1,2,3]triazole.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2 h
  2. customthe resulting precipitate removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified by flash column chromatography (ethyl acetate 100%)

Quellen und Nachweise

ORD-Eintrag
ord-f64892ae18c344a4b8f049209f3376eb
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205326B2

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