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

HRID 2113891Notes

Reaction equation

HRID 2113891 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13]Cl)=[C:9]([F:15])[CH:8]=1)[CH:4]=[CH2:5].[N:16]1([CH2:21][CH2:22][OH:23])[CH:20]=[CH:19][N:18]=[N:17]1.O>CN(C=O)C>[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:23][CH2:22][CH2:21][N:16]2[CH:20]=[CH:19][N:18]=[N:17]2)=[C:9]([F:15])[CH:8]=1)[CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 99892372-(1H-1,2,3-triazol-1-yl)ethan-1-olHCID 692933781-Allyloxy-3-fluoro-4-chloromethyl-benzene

Product 1

HCID 692938261-[2-(4-allyloxy-2-fluoro-benzyloxy)-ethyl]-1H-[1,2,3]triazoleYield 103.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

816 mg (32.3 mmol) 95% Sodium hydride were given at −50° C. to a solution of 4.32 g (21.5 mmol) 1-allyloxy-3-fluoro-4-chloromethyl-benzene and 2.51 g (22.2 mmol) 2-(1H-[1,2,3]-triazol-1-yl)-ethanol in 30 ml DMF. The mixture was allowed to warm slowly to r.t., stirred overnight and 10 ml water added. The mixture was extracted twice with ethyl acetate, and the combined organic phases dried over Na2SO4. Solvents were removed in vacuum to yield 6.18 g 1-[2-(4-allyloxy-2-fluoro-benzyloxy)-ethyl]-1H-[1,2,3]triazole yellow oil that was used without further purification.

Workup

  1. extractionThe mixture was extracted twice with ethyl acetate
  2. dry with materialthe combined organic phases dried over Na2SO4
  3. customSolvents were removed in vacuum

Sources & evidence

ORD record
ord-860e3c1e0b61451a8a1cb31e50b10533
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

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