1H-1,2,4-Triazole → Ethyl 6-[p-[5-(1,2,4-triazol-1-yl)pentyloxy]phenoxy]-2,2-dimethylhexanoate

HRID 329467Notes

Reaction equation

HRID 329467 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:26]=[CH:25][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([CH3:24])([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:10][CH:9]=1.[Na].[NH:28]1[CH:32]=[N:31][CH:30]=[N:29]1>CN(C=O)C>[N:28]1([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]2[CH:26]=[CH:25][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([CH3:24])([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:10][CH:9]=2)[CH:32]=[N:31][CH:30]=[N:29]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 5360545SodiumHCID 14851566Ethyl 6-[p-(5-bromopentyloxy)phenoxy]-2,2-dimethylhexanoate

Product 1

HCID 14327307Ethyl 6-[p-[5-(1,2,4-triazol-1-yl)pentyloxy]phenoxy]-2,2-dimethylhexanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.16 g ethyl 6-[p-(5-bromopentyloxy]phenoxy)-2,2-dimethylhexanoate in 10 ml DMF, was added with stirring 0.55 g sodium salt of 1,2,4-triazole at room temperature, and stirring was continued overnight. DMF was distilled off under reduced pressure, the residue was extracted with chloroform, and the extract was washed with water, dried and concentrated. The crude product thus obtained was purified by silica gel column chromatography, affording 1.21 g of ethyl 6-[p-[5-(1,2,4-triazol-1-yl)pentyloxy]phenoxy]-2,2-dimethylhexanoate.

Workup

  1. distillationDMF was distilled off under reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washthe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product thus obtained
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b822d86399a74df8b5387cc9d1022eb9
Source dataset
uspto-grants-1990_01
Patent number
US04891432

Reaction notes

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