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

HRID 839272Notes

Reaction equation

HRID 839272 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-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In an argon atmosphere, the unpurified 2-diazo-3-oxo-6-heptenoic acid methyl ester of Preparation 1 (4.55 g, 25 mmol) was dissolved in 100 ml of benzene. Anhydrous cupric sulfate (2.5 g) was added as a catalyst to the solution. The mixture was stirred for about 3 hours under reflux. After confirming the disappearance of the starting materials by thin layer chromatography, the reaction mixture was filtered through a Celite column. The solvvent was distilled off from the filtrate under reduced pressure and the remaining oily product was distilled under a reduced pressure to obtain 2.92 g of 2-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester as an oily product.

Workup

  1. temperatureunder reflux
  2. filtrationthe reaction mixture was filtered through a Celite column
  3. distillationThe solvvent was distilled off from the filtrate under reduced pressure
  4. distillationthe remaining oily product was distilled under a reduced pressure

Sources & evidence

ORD record
ord-0cc16c37c0cb48978a3656f7ce696e44
Source dataset
uspto-grants-1978_06
Patent number
US04094886

Reaction notes

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