HCID 53993450, compound → HCID 21835145, compound

HRID 1741285Notes

Reaction equation

HRID 1741285 reaction equation
C[O:2][CH:3]=[C:4]([C:6]1[N:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:5]>C1COCC1.O.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH:4]([CH3:5])[CH:3]=[O:2])[N:7]=1

Participants

5

Reactant 1

HCID 53993450HCID 53993450, compound

Product 1

HCID 21835145HCID 21835145, compoundYield 23.1%

Reagents, catalysts & solvents 3

HCID 15337Mercuric acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methoxy-2-(pyridazin-3-yl)propene (0.26 g, 1.72 mmol) in THF (50 ml) and water (10 ml) under nitrogen at ambient temperature was added mercury(II)acetate (1.66 g, 5.2 mmol). This mixture was stirred at room temperature for 2 hours, and was then poured onto potassium iodide solution (7%, 350 ml) and extracted with toluene (2×50 ml). The combined organic phases were washed with potassium iodide (7%, 140 ml) and brine (90 ml), dried (Na2SO4) and evaporated to give the title compound (54 mg, 23%), as an orange gum. The crude aldehyde was used directly without further purification.

Workup

  1. additionwas then poured onto potassium iodide solution (7%, 350 ml)
  2. extractionextracted with toluene (2×50 ml)
  3. washThe combined organic phases were washed with potassium iodide (7%, 140 ml) and brine (90 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-3822291380ff4127aecad5f09c26e236
Source dataset
uspto-grants-1999_10
Patent number
US05973156

Reaction notes

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