Ethyl diazoacetate → HCID 53828457, compound

HRID 1590601Notes

Reaction equation

HRID 1590601 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[N+:7](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N-:8]>CCOCC>[CH:1]1([C:4](=[O:5])[C:9](=[N+:7]=[N-:8])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 53828457HCID 53828457, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cyclopropanecarbonyl chloride (36 g, 0.34 mol) was added dropwise to a stirred solution of ethyl diazoacetate (86.2 g, 0.76 mol) in dry ether (500 ml) at 0° C. under a nitrogen atmosphere. The mixture was allowed to warm to room temperature then was stirred for 1 day, heated to gentle reflux for 2 days, then left to stand at room temperature for 5 days. Evaporation of the mixture followed by distillation afforded ethyl 3-cyclopropyl-2-diazo-3-oxo-propanoate (27.4 g, 44%) bp 85°-90° at 1 mm Hg).

Workup

  1. temperatureheated
  2. temperatureto gentle reflux for 2 days
  3. waitleft
  4. waitto stand at room temperature for 5 days
  5. customEvaporation of the mixture
  6. distillationfollowed by distillation

Sources & evidence

ORD record
ord-80fd103b170548c9b74d014178e6a555
Source dataset
uspto-grants-1993_04
Patent number
US05204333

Reaction notes

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