Potassium trimethylsilanolate → HCID 58198667, compound

HRID 545319Notes

Reaction equation

HRID 545319 reaction equation
C([O:3][C:4](=[O:18])[C:5]([S:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[F:17])([CH3:7])[CH3:6])C.C[Si](C)(C)[O-].[K+]>C1COCC1>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([S:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:18])=[O:3])=[C:10]([F:17])[CH:11]=1)#[N:16]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 58198617HCID 58198617, compound

Product 1

HCID 58198667HCID 58198667, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.1 g (4.1 mmol) of 2-(4-cyano-2-fluoro -phenylsulfanyl)-2-methyl-propionic acid ethyl ester in THF (50 mL) were added 1.58 g (12.3 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 1.04 g of 2-(4-cyano-2-fluoro-phenylsulfanyl)-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-66b67d2fbe3647f786bde9f9fd456eea
Source dataset
uspto-grants-2011_05
Patent number
US07935715B2

Reaction notes

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