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

HRID 370564Notes

Reaction equation

HRID 370564 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-5d2c72f3fff8409dbd9c1050b719bf40
Source dataset
uspto-grants-1985_07
Patent number
US04526987

Reaction notes

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