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

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

Reactant 4

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 99892372-(1H-1,2,3-triazol-1-yl)ethan-1-ol

HCID 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.