Potassium Carbonate → Ethyl 3-ethynylbenzoate

HRID 1760088Notes

Reaction equation

HRID 1760088 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si]([C:11]#[C:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])(C)C>C(O)C>[C:12]([C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])#[CH:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22600505Ethyl 3-((trimethylsilyl)ethynyl)benzoate

Product 1

HCID 15540684Ethyl 3-ethynylbenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium carbonate (583 mg, 4.22 mmol) was added to an ethanol solution (10 ml) of ethyl 3-[(trimethylsilyl)ethynyl]benzoate (1.04 g, 4.22 mmol), and stirred at room temperature for 2 h. The mixture was concentrated, and the residue was dissolved in ethyl acetate. The organic layer was washed with water and then brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=30/1) to give ethyl 3-ethynylbenzoate (96%).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine, dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=30/1)

Sources & evidence

ORD record
ord-2ae273aae2844941bfd776dcc30f0715
Source dataset
uspto-grants-2005_01
Patent number
US06838574B1

Reaction notes

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