Diazomethane → 1-Diazonio-3,3-dimethylbut-1-en-2-olate

HRID 2085365Notes

Reaction equation

HRID 2085365 reaction equation
[N+:1](=[CH2:3])=[N-:2].[CH3:4][C:5]([CH3:10])([CH3:9])[C:6](Cl)=[O:7]>CCOCC>[N+:1](=[CH:3][C:6](=[O:7])[C:5]([CH3:10])([CH3:9])[CH3:4])=[N-:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 62493Pivaloyl chloride

Product 1

HCID 217927841-Diazonio-3,3-dimethylbut-1-en-2-olate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the diazomethane solution was added a solution of trimethylacetyl chloride (15 mL, 0.12 mol) in ether (100 mL) dropwise over 40 minutes. After addition was complete, the solution was allowed to warm slowly overnight to room temperature. The solution was purged with a flow of nitrogen gas to remove any excess diazomethane and the resulting solution was concentrated to give 1-diazo-3,3-dimethyl-2-butanone as a yellow oil which was used directly in the next step.

Workup

  1. additionAfter addition
  2. temperatureto warm slowly overnight to room temperature
  3. customThe solution was purged with a flow of nitrogen gas
  4. customto remove any excess diazomethane
  5. concentrationthe resulting solution was concentrated

Sources & evidence

ORD record
ord-996df5c72a8b4680b71561a3547cd544
Source dataset
uspto-grants-2004_04
Patent number
US06720347B2

Reaction notes

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