Potassium Carbonate → HCID 15853364, compound

HRID 1760085Notes

Reaction equation

HRID 1760085 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si](C)(C)[C:9]#[C:10]/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[C:13]([O:15][CH2:16][CH3:17])(=[O:14])/[CH:12]=[CH:11]/[C:10]#[CH:9]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 12398706HCID 12398706, compound

Product 1

HCID 15853364HCID 15853364, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium carbonate (563 mg, 4.07 mmol) was added to a solution of ethyl 5-trimethylsilyl-(E)-2-penten-4-ynoate(800 mg, 4.07 mmol) in ethanol (10 ml), and the mixture was stirred at room temperature for 1 h. The reaction was quenched by the addition of 2N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel flash column chromatography to give ethyl (E)-2-penten-4-ynoate (79%).

Workup

  1. customThe reaction was quenched by the addition of 2N hydrochloric acid
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-26f93864804b49b3871a3db58f68f89e
Source dataset
uspto-grants-2005_01
Patent number
US06838574B1

Reaction notes

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