Trifluoroacetic acid → Ethyl 2-[(cyclopropyloxy)imino]-3-oxobutanoate

HRID 1074333Notes

Reaction equation

HRID 1074333 reaction equation
[CH:1]1([O:4][N:5]=[C:6]([C:12]2(OCC[O:14]2)[CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl.C(OCC)C>[CH:1]1([O:4][N:5]=[C:6]([C:12](=[O:14])[CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53725137HCID 53725137, compound

Product 1

HCID 54259708Ethyl 2-[(cyclopropyloxy)imino]-3-oxobutanoateYield 95.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-cyclopropyloxyimino-3,3-ethylenedioxybutyrate (syn isomer)(487 mg) in methylene chloride (0.8 ml) was added 90% trifluoroacetic acid (0.8 ml) under ice-cooling. The mixture was stirred at ambient temperature for 2 hours. The mixture was concentrated in vacuo to give a residue. The residue was dissolved in diethyl ether and washed successively with saturated aqueous solution of sodium bicarbonate and water, dried over magnesium sulfate and concentrated in vacuo to give ethyl 2-cyclopropyloxyimino-3-oxobutyrate (syn isomer)(382 mg) as an oil.

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give a residue
  4. washwashed successively with saturated aqueous solution of sodium bicarbonate and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3663d7e9098443d8b048cda474d562b3
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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