Chlorotrimethylsilane → 4-Methyl-2-trimethylsilylthiazole

HRID 975039Notes

Reaction equation

HRID 975039 reaction equation
C([Li])CCC.[CH3:6][C:7]1[N:8]=[CH:9][S:10][CH:11]=1.[CH3:12][Si:13](Cl)([CH3:15])[CH3:14]>C(OCC)C>[CH3:6][C:7]1[N:8]=[C:9]([Si:13]([CH3:15])([CH3:14])[CH3:12])[S:10][CH:11]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 127484-MethylthiazoleHCID 178418339Butyllithium

Product 1

HCID 116583544-Methyl-2-trimethylsilylthiazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

n-Butyllithium (2.5M solution in hexane, 1.1 equivalents) was added dropwise to a solution of 4-methylthiazole (1.0 equivalent) in dry diethyl ether at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, trimethylsilylchloride (1.0 equivalent) was added dropwise. The mixture was allowed to warm to room temperature and was then quenched by the addition of saturated aqueous sodium hydrogen carbonate. Work-up in the normal fashion and vacuum distillation then gave the title compound. B.p. 42° C. at 1 mm Hg.

Workup

  1. customwas then quenched by the addition of saturated aqueous sodium hydrogen carbonate
  2. distillationWork-up in the normal fashion and vacuum distillation

Sources & evidence

ORD record
ord-70ac4226f26d4a2cb81871265b0b127a
Source dataset
uspto-grants-1997_03
Patent number
US05607956

Reaction notes

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