Chlorotrimethylsilane → 2-Trimethylsilylthiazole

HRID 1915587Notes

Reaction equation

HRID 1915587 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH3:11][Si:12](Cl)([CH3:14])[CH3:13]>C(OCC)C>[CH3:11][Si:12]([CH3:14])([CH3:13])[C:7]1[S:6][CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 9256ThiazoleHCID 178418339Butyllithium

Product 1

HCID 5884532-Trimethylsilylthiazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-70 °C

Procedure

To a mixture of 40.6 ml n-butyl lithium (1.6M in hexane) and 18 ml diethylether is added dropwise at −70° C. a solution of 5.03 g thiazole dissolved in 59 ml diethylether. After 30 min 6.41 g trimethylsilylchloride dissolved in 59 ml diethylether is added at −70° C. The reaction mixture is stirred at −70° C. for 1 h and allowed to warm up to room temperature. The mixture is washed with saturated NaHCO3 solution, dried over Na2SO4 and the solvent is evaporated. The residue is distilled, to yield the desired product.

Workup

  1. additionis added at −70° C
  2. temperatureto warm up to room temperature
  3. washThe mixture is washed with saturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated
  6. distillationThe residue is distilled

Sources & evidence

ORD record
ord-43e318f396d34e59ae4d5aa0fbd7dce1
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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