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

HRID 1271423Notes

Reaction equation

HRID 1271423 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 184535171-[2-(4-nitro-benzyloxy)-ethyl]-1H-[1,2,3]triazoleYield 27.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-f64892ae18c344a4b8f049209f3376eb
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

Loading…