Potassium fluoride dihydrate → Methyl(4-cyano-6-hydroxy-1-benzothiophen-3-yl)acetate

HRID 591557Notes

Reaction equation

HRID 591557 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[C:9]2[C:10]([C:25]#[N:26])=[CH:11][C:12]([O:14][Si](C(C)C)(C(C)C)C(C)C)=[CH:13][C:8]=2[S:7][CH:6]=1.O.O.[F-].[K+]>CCO>[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[C:9]2[C:10]([C:25]#[N:26])=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1

Participants

4

Reactant 2

HCID 23708904Potassium fluoride dihydrateHCID 131734534Methyl(4-cyano-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 125474215Methyl(4-cyano-6-hydroxy-1-benzothiophen-3-yl)acetateYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl(4-cyano-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate (1.92 g) and EtOH (30 mL) was added potassium fluoride dihydrate (0.448 g) at room temperature, and the mixture was refluxed for 30 min. The mixture was concentrated under reduced pressure. The residue was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with 0.1N HCl and brine, dried over MgSO4 and concentrated in vacuo. The residue was crystallized from EtOAc-hexane to give the title compound (0.935 g).

Workup

  1. temperaturethe mixture was refluxed for 30 min
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionThe residue was poured into water at room temperature
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed successively with 0.1N HCl and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-1b29185503304ead9a42513790b53ca7
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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