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

HRID 1060248Notes

Reaction equation

HRID 1060248 reaction equation
[N+:1](=[CH2:3])=[N-:2].[CH3:4][C:5]([CH3:10])([CH3:9])[C:6](Cl)=[O:7]>C(OCC)C>[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-olateYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the diazomethane solution at 0° C. was added a solution of 1.23 mL (1.21 g, 10 mmol, Aldrich) of trimethylacetyl chloride in 1 mL of diethyl ether dropwise with stirring. The resulting mixture was kept at 0° C. for 16 h. The solution was sparged with argon to remove the excess diazomethane and diethyl ether was removed under reduced pressure to give 1.33 g (10 mmol, 100%) of crude 1-diazo-3,3-dimethyl-2-butanone as a yellow liquid.

Workup

  1. customThe solution was sparged with argon
  2. customto remove the excess diazomethane and diethyl ether
  3. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-5fc5b7415a664aa2b8b4165b60725760
Source dataset
uspto-grants-2003_02
Patent number
US06521759B2

Reaction notes

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