HCID 19744589, compound → HCID 19744627, compound

HRID 2254415Notes

Reaction equation

HRID 2254415 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[C:9](OCC)=[O:10])[CH:5]=[N:4][N:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.O1CCOCC1>[OH:10][CH2:9][C:8]1[CH:7]=[C:6]([N:1]2[CH:2]=[N:3][N:4]=[CH:5]2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 19744589HCID 19744589, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19744627HCID 19744627, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

430 mg of ethyl 3-(1,3,4-triazol-1-yl)benzoate [synthesized substantially in accordance with the method described in J. Med. Chem., 5, 383 (1962)] was dissolved in a mixture of 20 ml of tetrahydrofuran and 20 ml of dioxane, and 100 mg of lithium aluminium hydride was added. The mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was distributed between ethyl acetate and water. The organic layer was separated and dried over anhydrous sodium sulfate. The desiccant was separated by filtration, and the solvent evaporated. The residue was purified by silica gel column chromatography [Wakogel C-200, 20 g; eluting solvent: chloroform/methanol=20/1] to give 240 mg (yield 69%) of 1(3-hydroxymethylphenyl)-1,3,4-triazole.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe desiccant was separated by filtration
  6. customthe solvent evaporated
  7. customThe residue was purified by silica gel column chromatography [Wakogel C-200, 20 g; eluting solvent: chloroform/methanol=20/1]

Sources & evidence

ORD record
ord-a29c444c0fac40a7a8ea1d18f4247b3f
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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