Triethylamine → 1-Trichloromethyl-3-methyl-2-butenyl 2-diazoacetoacetate

HRID 127036Notes

Reaction equation

HRID 127036 reaction equation
[C:1]([O:7][CH:8]([C:13]([Cl:16])([Cl:15])[Cl:14])[CH:9]=[C:10]([CH3:12])[CH3:11])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C(N(CC)CC)C.S(N=[N+]=[N-])([N:27]=[N+:28]=[N-])(=O)=O>C(#N)C>[N+:27](=[C:2]([C:3]([CH3:5])=[O:4])[C:1]([O:7][CH:8]([C:13]([Cl:14])([Cl:15])[Cl:16])[CH:9]=[C:10]([CH3:11])[CH3:12])=[O:6])=[N-:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 125252031-Trichloromethyl-3-methyl-2-butenyl acetoacetateHCID 15191028Sulfuryl diazide

Product 1

HCID 544620301-Trichloromethyl-3-methyl-2-butenyl 2-diazoacetoacetateYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-trichloromethyl-3-methyl-2-butenyl acetoacetate (0.575 g, 2 mmole) and triethylamine (0.404 g, 4 mmole) in 10 ml of acetonitrile was added 1 g of polymer-bound sulfonyl azide (prepared by the method of Roush, et al., loc. cit.). The mixture was stirred overnight at room temperature and filtered. The filter cake was washed with ether, and the slurry was filtered. Solvent was removed by evaporation from the combined filtrates to give 1-trichloromethyl-3-methyl-2-butenyl 2-diazoacetoacetate (0.60 g, 96% yield).

Workup

  1. customprepared by the method of Roush, et al., loc
  2. filtrationfiltered
  3. washThe filter cake was washed with ether
  4. filtrationthe slurry was filtered
  5. customSolvent was removed by evaporation from the combined filtrates

Sources & evidence

ORD record
ord-b5578ddb514340cf8d52ac1ad8d4781d
Source dataset
uspto-grants-1981_03
Patent number
US04254282

Reaction notes

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