Potassium Carbonate → 1-[4-(4-benzyloxyphenyl)butyl)-1H-1,2,3-triazole

HRID 2084370Notes

Reaction equation

HRID 2084370 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.[NH:20]1[CH:24]=[CH:23][N:22]=[N:21]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:20]2[CH:24]=[CH:23][N:22]=[N:21]2)=[CH:7][CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22259342Benzyl 4-(4-iodobutyl)phenyl etherHCID 178418936HCID 178418936, compound

Product 1

HCID 227333491-[4-(4-benzyloxyphenyl)butyl)-1H-1,2,3-triazoleYield 42.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Benzyl 4-(4-iodobutyl)phenyl ether (1.1 g), 1H-1,2,3-triazole (0.31 g), and potassium carbonate (0.622 g) were suspended in DMF (7.5 ml), followed by stirring at 70° C. for 26.5 hours. After cooling, the reaction mixture was extracted with ethyl acetate and washed with water and saturated saline. Under reduced pressure, the solvent was distilled off; the residue was subjected to silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:3) to yield the titled compound (0.391 g).

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washwashed with water and saturated saline
  4. distillationUnder reduced pressure, the solvent was distilled off

Sources & evidence

ORD record
ord-4017f839441f42908f0a339695075be8
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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