Trifluoroacetic acid → Dipyrromethane

HRID 2066085Notes

Reaction equation

HRID 2066085 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:6](O)([C:8](F)(F)F)=O>C(OCC)(=O)C>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:3][C:2]1[NH:1][CH:5]=[CH:6][CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 8027Pyrrole

Product 1

HCID 140814DipyrromethaneYield 381.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of p-formaldehyde (1100 mg, 35 mmol) in pyrrole (50 ml, 720 mmol), at 50° C., TFA (416 mg, 3.5 mmol) was added. The reaction mixture was kept under magnetic stirring, at room temperature, for 30 minutes, then ethyl acetate was added and the solution washed with NaHCO3 saturated solution, then the organic phase was dried on Na2SO4. After evaporation the crude product was purified by chromatography on silica gel (Petroleum Ether/Ethyl acetate 4/1+1% TEA). 1950 mg (yield 38%) of the product were obtained.

Workup

  1. washthe solution washed with NaHCO3 saturated solution
  2. customthe organic phase was dried on Na2SO4
  3. customAfter evaporation the crude product
  4. customwas purified by chromatography on silica gel (Petroleum Ether/Ethyl acetate 4/1+1% TEA)

Sources & evidence

ORD record
ord-bd9c0020429e461aa550e67b2faab5e0
Source dataset
uspto-grants-2012_10
Patent number
US08288528B2

Reaction notes

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