Imidazole → 3-(Tertbutyldimethylsilyloxy)-1-(1,2,4-triazol-1-yl)propane

HRID 454112Notes

Reaction equation

HRID 454112 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][OH:9])[CH:5]=[N:4][CH:3]=[N:2]1.[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:10]([Si:14]([CH3:16])([CH3:15])[O:9][CH2:8][CH2:7][CH2:6][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1)([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 47118023-(1H-1,2,4-triazol-1-yl)propan-1-ol

Product 1

HCID 220308973-(Tertbutyldimethylsilyloxy)-1-(1,2,4-triazol-1-yl)propaneYield 84%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(1,2,4-triazol-1-yl)propan-1-ol (7 g, 55 mmol) in DMF (70 ml) was added tertbutyldimethylsilyl chloride (9.1 g, 60 mmol) followed by DMAP (336 mg, 2.7 mmol) followed by imidazole (4.5gr, 66 mmol). After stirring overnight at ambient temperature, the volatiles were removed under vacuum and the residue was partitioned between water and ethyl acetate/ether. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluting with methylene chloride/ether (6/4) to give 3-(tertbutyldimethylsilyloxy)-1-(1,2,4-triazol-1-yl)propane (11.1 gr, 84%).

Workup

  1. customthe volatiles were removed under vacuum
  2. customthe residue was partitioned between water and ethyl acetate/ether
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with methylene chloride/ether (6/4)

Sources & evidence

ORD record
ord-024284ce831e40c1a215f56582a77156
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

Loading…