Trichloroisocyanuric Acid → 1-(5-Isopropoxypyridin-2-yl)ethanone

HRID 1038543Notes

Reaction equation

HRID 1038543 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([OH:13])[CH3:12])=[N:9][CH:10]=1)[CH3:3].CC1(C)N([O])C(C)(C)CCC1.ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>CC(C)=O>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11](=[O:13])[CH3:12])=[N:9][CH:10]=1)[CH3:1]

Participants

5

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 2724126TempoHCID 665985281-[5-(1-Methylethoxy)pyridin-2-yl]ethanol

Product 1

HCID 581262881-(5-Isopropoxypyridin-2-yl)ethanoneYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

1-[5-(1-Methylethoxy)pyridin-2-yl]ethanol (22 mg, 0.119 mmol) was dissolved in acetone (1.2 mL), added 2,2,6,6-tetramethylpiperidine 1-oxyl (2.0 mg, 0.012 mmol) and trichloroisocyanuric acid (30 mg, 0.131 mmol) under ice-cold conditions, and the mixture was stirred at 0° C. for 10 minutes. The reaction solution was concentrated in vacuo, added an aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and 1-[5-(1-methylethoxy)pyridin-2-yl]ethanone (20 mg (yield 94%)) was obtained as a yellow oil.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additionadded an aqueous solution of sodium hydrogen carbonate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over 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-8435abb596f74828b6152d07e971ffba
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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