Dimethylformamide → 1-[2-(4-Allyloxy-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]triazole

HRID 2113885Notes

Reaction equation

HRID 2113885 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13]Cl)=[CH:9][C:8]=1C)[CH:4]=[CH2:5].[N:16]1([CH2:21][CH2:22][OH:23])[CH:20]=[CH:19][N:18]=[N:17]1.[CH3:24]N(C=O)C>>[CH2:3]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][O:23][CH2:22][CH2:21][N:16]2[CH:20]=[CH:19][N:18]=[N:17]2)=[C:11]([CH3:24])[CH:12]=1)[CH:4]=[CH2:5]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 99892372-(1H-1,2,3-triazol-1-yl)ethan-1-olHCID 222420771-Allyloxy-4-chloromethyl-2-methyl-benzene

Product 1

HCID 692933751-[2-(4-Allyloxy-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]triazoleYield 86%

Procedure

1.122 g (46.7 mmol) 95% Sodium hydride were given at −50° C. to a solution of 5.630 g (31.2 mmol) 1-allyloxy-4-chloromethyl-2-methyl-benzene and 3.525 g (31.2 mmol) 2-(1H-[1,2,3]-triazol-1-yl)-ethanol in DMF. The mixture was allowed to warm slowly to r. t., stirred for 5 hours. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4 and the solvent was distilled off under reduced pressure to yield 7.30 g (86%) 1-[2-(4-Allyloxy-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]triazole as yellow oil which was used without further purification.

Workup

  1. temperatureto warm slowly
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-125b9993e35d48ba8863cd6da0f22eda
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

Loading…