Chlorotrimethylsilane → 4-Methyl-2-trimethylsilylthiazole

HRID 2798

Reaction equation

HRID 2798 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 mmHg.

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-5a7b382c7d5a4739a7806a3eb2f4a308
Source dataset
uspto-grants-1998_03
Patent number
US05731335

Linked notes

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