Water → Ethyl 1-cyclobutene-1-carboxylate

HRID 1457969Notes

Reaction equation

HRID 1457969 reaction equation
[C:1]1([C:5]([OH:7])=[O:6])[CH2:4][CH2:3][CH:2]=1.[CH2:8](I)[CH3:9].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:8]([O:6][C:5]([C:1]1[CH2:4][CH2:3][CH:2]=1)=[O:7])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 11434914Cyclobut-1-ene-1-carboxylic acid

Product 1

HCID 22223228Ethyl 1-cyclobutene-1-carboxylateYield 108.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.2425 g (33.09 mmol) of 1-cyclobutenecarboxylic acid in 60 ml of dimethylformamide were added 12 ml (150 mmol) of ethyl iodide and 5.53 g (40 mmoL) of potassium carbonate, followed by 20 hours of stirring at room temperature. The reaction solution was poured into water and extracted with ether. The organic layer was washed with water and saturated brine and then dried over anhydrous sodium sulfate. By evaporating the solvent, 4.5267 g of the title compound was obtained as a mixture with ethyl iodide and ether.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customBy evaporating the solvent

Sources & evidence

ORD record
ord-1b2f6fa95d1f4c8387d29fba12d691d0
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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