Potassium Acetate → Ethyl 2-(1-benzyloxycarbonyl-3-azetidinyl)acrylate

HRID 1457998Notes

Reaction equation

HRID 1457998 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([CH:15]([C:21](O)=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[K+]>C(#N)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]([C:15](=[CH2:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 53765389Ethyl hydrogen (1-benzyloxycarbonyl-3-azetidinyl)malonate

Product 1

HCID 54322358Ethyl 2-(1-benzyloxycarbonyl-3-azetidinyl)acrylateYield 86.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 732 mg (2.28 mmol) of ethyl hydrogen (1-benzyloxycarbonyl-3-azetidinyl)malonate dissolved in 70 ml of acetonitrile were added 1.05 g (5.67 mmol) of Eshenmoser's salt and a catalytically effective amount of potassium acetate, followed by 4.5 hours of heating under reflux. After evaporation of the solvent, the resulting residue was mixed with 100 ml of ethyl acetate, washed with 10% citric acid aqueous solution, 10% sodium sulfite aqueous solution and saturated brine in that order, and then dried over anhydrous sodium sulfate. By evaporating the solvent, 569 mg (86%) of the title compound was obtained.

Workup

  1. additionwere added 1.05 g (5.67 mmol) of Eshenmoser's salt
  2. temperatureof heating
  3. temperatureunder reflux
  4. customAfter evaporation of the solvent
  5. additionthe resulting residue was mixed with 100 ml of ethyl acetate
  6. washwashed with 10% citric acid aqueous solution, 10% sodium sulfite aqueous solution and saturated brine in that order
  7. dry with materialdried over anhydrous sodium sulfate
  8. customBy evaporating the solvent

Sources & evidence

ORD record
ord-811ea7ee01dd4281abbeeec749354545
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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