Trichloroisocyanuric Acid → 5-Acetylfuro(2,3-c)pyridine

HRID 1038608Notes

Reaction equation

HRID 1038608 reaction equation
[O:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH:10]([OH:12])[CH3:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.CC1(C)N([O])C(C)(C)CCC1.C1(N(Cl)C(=O)N(Cl)C(=O)N1Cl)=O>CC(C)=O>[O:1]1[C:5]2=[CH:6][N:7]=[C:8]([C:10](=[O:12])[CH3:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 2724126TempoHCID 105112031-(Furo[2,3-c]pyridin-5-yl)ethanol

Product 1

HCID 97939025-Acetylfuro(2,3-c)pyridineYield 34%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(Furo[2,3-c]pyridin-5-yl)ethanol (356 mg, 2.19 mmol) was dissolved in acetone (11 mL), and added 2,2,6,6-tetramethylpiperidine 1-oxyl (34 mg, 220 μmol) at room temperature. Then, the reaction solution was added 1,3,5-trichloro-2,4,6-triazinetrione (560 mg, 2.41 mmol), and stirred at the same temperature for 30 minutes. The reaction solution was concentrated in vacuo, added water and a saturated aqueous solution of sodium hydrogen carbonate under ice-cold conditions, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (119 mg (yield 34%)) was obtained as a yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additionadded water
  3. extractiona saturated aqueous solution of sodium hydrogen carbonate under ice-cold conditions, and extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-950705b0187048489c86da0493783058
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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