2-Diazonio-1-methoxy-3-oxohepta-1,6-dien-1-olate → Methyl 2-oxobicyclo[3.1.0]hexane-1-carboxylate

HRID 866563Notes

Reaction equation

HRID 866563 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[N+]=[N-])[C:5](=[O:10])[CH2:6][CH2:7][CH:8]=[CH2:9]>C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:4]12[CH2:9][CH:8]1[CH2:7][CH2:6][C:5]2=[O:10])=[O:13]

Participants

3

Reactant 1

HCID 540756342-Diazonio-1-methoxy-3-oxohepta-1,6-dien-1-olate

Product 1

HCID 12881134Methyl 2-oxobicyclo[3.1.0]hexane-1-carboxylateYield 59,316.301%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In argon atmosphere, 2-diazo-3-oxo-6-heptenoic acid methyl ester (34 g, 0.187 mmol) was dissolved in benzene (300 ml). An acetyl acetone-copper complex (1 g) was added to the solution. The mixture was stirred for one night under refluxing. After cooling it, the solvent was distilled off under a reduced pressure. The residue was purified by a distillation to obtain 17.1 g of 2-oxo-bicyclo [3.1.0] hexane-1-carboxylic acid methyl ester. Yield: 60%. Boiling point: 83° to 85° C/0.3 mmHg.

Workup

  1. additionAn acetyl acetone-copper complex (1 g) was added to the solution
  2. temperatureunder refluxing
  3. temperatureAfter cooling it
  4. distillationthe solvent was distilled off under a reduced pressure
  5. distillationThe residue was purified by a distillation

Sources & evidence

ORD record
ord-d0d6e585298b4cf4bba53b15b054eb97
Source dataset
uspto-grants-1978_07
Patent number
US04100184

Reaction notes

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