Trichloroisocyanuric Acid → Furo[2,3-c]pyridine-5-carboxaldehyde

HRID 1038606Notes

Reaction equation

HRID 1038606 reaction equation
[O:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH2:10][OH:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.C1(N(Cl)C(=O)N(Cl)C(=O)N1Cl)=O>CC(C)=O.CC1(C)N([O])C(C)(C)CCC1>[O:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH:10]=[O:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 22047174Furo[2,3-c]pyridin-5-ylmethanol

Product 1

HCID 22047533Furo[2,3-c]pyridine-5-carboxaldehydeYield 95%

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 180AcetoneSolvent

Procedure

Furo[2,3-c]pyridin-5-yl methanol (521 mg, 3.49 mmol) was dissolved in acetone (17 mL), added 2,2,6,6-tetramethylpiperidine 1-oxyl (27 mg, 170 μmol) at room temperature. Then, the reaction solution was added 1,3,5-trichloro-2,4,6-triazinetrione (892 mg, 3.84 mmol) under ice-cold conditions, and stirred at the same temperature for 5 minutes. The reaction solution was concentrated in vacuo, added water and a saturated aqueous solution of sodium hydrogen carbonate under ice-cold conditions, 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 (488 mg (yield 95%)) 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, 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-ace3886d5c5444eeafb5e61c05a90299
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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