tert-Butanol → HCID 54093447, compound

HRID 1032464Notes

Reaction equation

HRID 1032464 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](C)[C:9](=[O:16])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:4][CH:3]=1.[I-].C[S+](C)(C)=O.[OH-].[K+].[NH:26]1[CH:30]=[N:29][CH:28]=[N:27]1.[C:31](O)(C)(C)[CH3:32]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([N:26]2[CH:30]=[N:29][CH:28]=[N:27]2)[C:9]([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)([OH:16])[CH2:31][CH3:32])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 6386tert-ButanolHCID 92571H-1,2,4-TriazoleHCID 14797Potassium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 22165696HCID 22165696, compound

Product 1

HCID 54093447HCID 54093447, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(4-chlorophenyl)1-(1,2,4-triazol-1-yl)butan-2-one (0.7g), trimethylsulphoxonium iodide (0.77g), potassium hydroxide (0.38g) and 1,2,4-triazole (0.24g) in tert butyl alcohol (lOml) was heated at reflux for 4h. The reaction mixture was cooled and poured into water, and the aqueous phase was separated and extracted with ethyl acetate. The organic extract was separated, dried and concentrated to dryness under reduced pressure, and the residue was purified by column chromatography on silica using 2% by volume methanol in chloroform as eluent, to give 3 (4 chlorophenyl)-1-(1,2,4-triazol-1-yl)-2(1,2,4-triazol-1-ylmethyl)butan-2-ol mp 60-64° .

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4h
  3. temperatureThe reaction mixture was cooled
  4. customthe aqueous phase was separated
  5. extractionextracted with ethyl acetate
  6. extractionThe organic extract
  7. customwas separated
  8. customdried
  9. concentrationconcentrated to dryness under reduced pressure
  10. customthe residue was purified by column chromatography on silica using 2% by volume methanol in chloroform as eluent

Sources & evidence

ORD record
ord-5753f2a8384945d8876229da04949a76
Source dataset
uspto-grants-1990_09
Patent number
US04957934

Reaction notes

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