Cesium fluoride → Methyl 2-ethynylbenzoate

HRID 424796

Reaction equation

HRID 424796 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[C:11][Si](C)(C)C.[F-].[Cs+]>C(#N)C.O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[CH:11]

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 11053512Methyl 2-((trimethylsilyl)ethynyl)benzoate

Product 1

HCID 373287Methyl 2-ethynylbenzoateYield 96.3%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of 2-trimethylsilanylethynyl-benzoic acid methyl ester (540 mg, 2.32 mmol) in acetonitrile/water (20 mL/5 mL) is added cesium fluoride (1.41 g, 9.30 mmol). The reaction is stirred at room temperature. After 4 h, the reaction is concentrated and the residue is partitioned between EtOAc (100 mL) and 0.2N HCl (30 mL). The aqueous layer is extracted with EtOAc (100 mL) and the combined organic layers are washed with brine, dried (MgSO4), filtered, and concentrated. The residue is chromatographed eluting with 0 to 5% EtOAc/Hexanes to yield the title compound (358 mg, 96%). GC/MS: 160.

Workup

  1. concentrationthe reaction is concentrated
  2. customthe residue is partitioned between EtOAc (100 mL) and 0.2N HCl (30 mL)
  3. extractionThe aqueous layer is extracted with EtOAc (100 mL)
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is chromatographed
  9. washeluting with 0 to 5% EtOAc/Hexanes

Sources & evidence

ORD record
ord-b2bc4d24489c4b2ca44e931528859e18
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Linked notes

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