Potassium trimethylsilanolate → HCID 58198507, compound

HRID 545322Notes

Reaction equation

HRID 545322 reaction equation
C([O:3][C:4](=[O:18])[C:5]([S:8]([C:11]1[CH:12]=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=1)(=[O:10])=[O:9])([CH3:7])[CH3:6])C.C[Si](C)(C)[O-].[K+]>C1COCC1>[Cl:17][C:14]1[N:13]=[CH:12][C:11]([S:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:18])=[O:3])(=[O:9])=[O:10])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 58198422HCID 58198422, compound

Product 1

HCID 58198507HCID 58198507, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 834 mg (2.86 mmol) of 2-(6-chloro-pyridine-3-sulfonyl)-2-methyl-propionic acid ethyl ester in THF (30 mL) were added 552 mg (4.3 mmol) of potassium trimethylsilanolate. The reaction was stirred at room temperature for 3 h. The solvent was removed under reduced pressure. The residue was partitioned between DCM (50 mL) and water (50 mL). The aqueous layer was acidified with 1 M aqueous HCl solution and extracted with DCM (4×50 mL). The combined organic extracts were dried over Na2SO4, filtered and the filtrate concentrated under reduced pressure to afford 661 mg of 2-(6-chloro-pyridine-3-sulfonyl)-2-methyl-propionic acid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was partitioned between DCM (50 mL) and water (50 mL)
  3. extractionextracted with DCM (4×50 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-5b613603d7074b75a7122e7af8ca4b7c
Source dataset
uspto-grants-2011_05
Patent number
US07935715B2

Reaction notes

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