Chlorotrimethylsilane → HCID 18925374, compound

HRID 1289052Notes

Reaction equation

HRID 1289052 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][CH:6]=1.C([Li])CCC.C[Si](Cl)(C)C.[C:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:19])[CH3:18].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([OH:19])[CH3:18]

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 7410AcetophenoneHCID 127484-MethylthiazoleHCID 516892Sodium BicarbonateHCID 178418339Butyllithium2×

Product 1

HCID 18925374HCID 18925374, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Methylthiazole (log) in dry tetrahydrofuran (50ml) at -70° C. was stirred under a nitrogen atmosphere and n-butyllithium (2.5M solution in hexane, 44.4 ml) was added dropwise. After 30 minutes, trimethylsilylchloride (12.8 ml) was added and the reaction mixture was allowed to warm to room temperature. After 30 minutes the mixture was cooled to -70° C. and n-butyllithium (44.4ml) was added dropwise. After 30 minutes, acetophenone (12.9ml) was added dropwise and the mixture stirred at -70° C. for 1 hour. The reaction mixture was allowed to warm to room temperature and aqueous sodium hydrogen carbonate was added. The organic layer was separated and the aqueous layer was extracted with diethylether. The combined organic layers were then worked up to afford the title compound as a white solid, m.p. 128.5-129.5° C.

Workup

  1. temperatureAfter 30 minutes the mixture was cooled to -70° C.
  2. waitAfter 30 minutes
  3. temperatureto warm to room temperature
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with diethylether

Sources & evidence

ORD record
ord-25101695ea5c43c583fe899a3253bdd7
Source dataset
uspto-grants-1998_05
Patent number
US05747515

Reaction notes

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