Potassium Carbonate → 1-(2,4-Difluorophenyl)-2-[3-(4-methoxystyryl)-1,2,4-triazol-1-yl]-1-(1,2,4-triazol-1-ylmethyl)ethanol

HRID 1650799Notes

Reaction equation

HRID 1650799 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH2:19][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1)([OH:18])[CH2:10][N:11]1[CH:15]=[N:14][C:13]([CH:16]=O)=[N:12]1.[Cl-].[CH3:26][O:27][C:28]1[CH:53]=[CH:52][C:31]([CH2:32][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH2:19][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1)([OH:18])[CH2:10][N:11]1[CH:15]=[N:14][C:13]([CH:16]=[CH:32][C:31]2[CH:30]=[CH:29][C:28]([O:27][CH3:26])=[CH:53][CH:52]=2)=[N:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2773651(4-Methoxybenzyl)triphenylphosphonium chlorideHCID 230524941-(2,4-Difluorophenyl)-2-(3-formyl-1,2,4-triazol-1-yl)-1-(1,2,4-triazol-1-ylmethyl)ethanol

Product 1

HCID 539864021-(2,4-Difluorophenyl)-2-[3-(4-methoxystyryl)-1,2,4-triazol-1-yl]-1-(1,2,4-triazol-1-ylmethyl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(2,4-difluorophenyl)-2-(3-formyl-1,2,4-triazol-1-yl)-1-(1,2,4-triazol-1-ylmethyl)ethanol (0.6 g), p-methoxybenzyl-triphenylphosphonium chloride (1.68 g), potassium carbonate (0.5 g) and methanol (10 ml) was heated at 60°-70° for 2 hours, then left at room temperature for 20 hours. The reaction mixture was filtered, the separated solids were washed with methanol, and the combined organic solutions were evaporated to dryness. The residue was purified by medium pressure liquid chromatography on silica, eluting with chloroform, to give 1-(2,4-difluorophenyl)-2-[3-(4-methoxystyryl)-1,2,4-triazol-1-yl]-1-(1,2,4-triazol-1-ylmethyl)ethanol, m.p. 150°-152°.

Workup

  1. temperaturewas heated at 60°-70° for 2 hours
  2. filtrationThe reaction mixture was filtered
  3. washthe separated solids were washed with methanol
  4. customthe combined organic solutions were evaporated to dryness
  5. customThe residue was purified by medium pressure liquid chromatography on silica
  6. washeluting with chloroform

Sources & evidence

ORD record
ord-2d8abce49207461e8123b51ecf3c0915
Source dataset
uspto-grants-1990_05
Patent number
US04925863

Reaction notes

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