Ammonium fluoride → 5-Methyl-1H-1,2,4-triazole-1-propanol

HRID 454114Notes

Reaction equation

HRID 454114 reaction equation
[F-].[NH4+].C([Si](C)(C)[O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16]([CH3:17])=[N:15][CH:14]=[N:13]1)(C)(C)C>CO>[CH3:17][C:16]1[N:12]([CH2:11][CH2:10][CH2:9][OH:8])[N:13]=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 25516Ammonium fluorideHCID 220308553-(Tertbutyldimethylsilyloxy)-1-(5-methyl-[1,2,4]-triazol-1-yl)propane

Product 1

HCID 220306985-Methyl-1H-1,2,4-triazole-1-propanolYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of ammonium fluoride (10.4 g, 280 mmol) in methanol (110 ml) was added a solution of 3-(tertbutyldimethylsilyloxy)-1-(5-methyl-[1,2,4]-triazol-1-yl)propane (7.2 g, 28 mmol) in methanol (30 ml). The mixture was refluxed for 4.5 hours. After cooling, silica (100 g) was added and the volatiles were removed under vacuum. The residue was added onto a column of silica and eluted with a mixture of methylene chloride/ethyl acetate (1/1) followed by methylene chloride/methanol (9/1) to give 3-(5-methyl-[1,2,4]-triazol-1-yl)propan-1-ol (3.65 g, 92%).

Workup

  1. temperatureThe mixture was refluxed for 4.5 hours
  2. temperatureAfter cooling
  3. additionsilica (100 g) was added
  4. customthe volatiles were removed under vacuum
  5. additionThe residue was added onto a column of silica
  6. washeluted with a mixture of methylene chloride/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-32a6c46cad244fe7be5ad11705e809f1
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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