Methyl iodide → 3-(Tertbutyldimethylsilyloxy)-1-(5-methyl-[1,2,4]-triazol-1-yl)propane

HRID 454113Notes

Reaction equation

HRID 454113 reaction equation
[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[N:13][CH:12]=[N:11]1)([CH3:4])([CH3:3])[CH3:2].[CH2:17]([Li])CCC.CI.[Cl-].[NH4+]>CN(C=O)C.CCOCC.C(OCC)(=O)C>[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]([CH3:17])=[N:13][CH:12]=[N:11]1)([CH3:2])([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 220308973-(Tertbutyldimethylsilyloxy)-1-(1,2,4-triazol-1-yl)propaneHCID 178418339Butyllithium

Product 1

HCID 220308553-(Tertbutyldimethylsilyloxy)-1-(5-methyl-[1,2,4]-triazol-1-yl)propaneYield 98%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of 3-(tertbutyldimethylsilyloxy)-1-(1,2,4-triazol-1-yl)propane (7 g, 29 mmol) in DMF (100 ml) cooled at −70° C. was added 2.5M n-butyllithium (17.4 ml) over 45 minutes. After stirring for 90 minutes at −70° C., methyl iodide (3.6 ml, 58 mmol) was added. After stirring for 2 hours at ambient temperature, the mixture was poured onto saturated ammonium chloride. The mixture was then diluted with ether and ethyl acetate. The organic layer was separated, washed with aqueous sodium thiosulphate followed by brine, dried (MgSO4) and evaporated to give 3-(tertbutyldimethylsilyloxy)-1-(5-methyl-[1,2,4]-triazol-1-yl)propane (7.3 g, 98%).

Workup

  1. stirringAfter stirring for 2 hours at ambient temperature
  2. customThe organic layer was separated
  3. washwashed with aqueous sodium thiosulphate
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d38978b4d4294d619f9d4a4a3c7f0456
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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