Potassium Carbonate → 1-(4-vinylphenyl)-1H-1,2,4-triazole

HRID 587279Notes

Reaction equation

HRID 587279 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[C:14]([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:10]([C:9]1[CH:12]=[CH:13][C:6]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:7][CH:8]=1)=[CH2:14]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 27764884-(1H-1,2,4-triazol-1-yl)benzaldehyde

Product 1

HCID 585499641-(4-vinylphenyl)-1H-1,2,4-triazoleYield 63%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 4-[1,2,4]triazol-1-yl-benzaldehyde (9.0 g, 52 mmol) in 1,4-dioxane (100 mL), were added K2CO3 (10.76 g, 78 mmol) and methyl triphenyl phosphonium bromide (22.2 g, 62.4 mmol) at room temperature. The resultant reaction mixture was heated to 70° C. for 18 h. After completion of the reaction (TLC), the reaction mixture was cooled to room temperature and filtered and the obtained filtrate was concentrated under reduced pressure. Purification by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in petroleum ether) to afforded the title compound as a white solid (5.6 g, 63%): ESIMS m/z 172.09 ([M+H]+).

Workup

  1. customThe resultant reaction mixture
  2. customAfter completion of the reaction (TLC)
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. concentrationthe obtained filtrate was concentrated under reduced pressure
  6. customPurification by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-fe847d70974148339b22c6d94828fdad
Source dataset
uspto-grants-2016_01
Patent number
US09226500B2

Reaction notes

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