Trichloroisocyanuric Acid → 5-Isopropoxypicolinaldehyde

HRID 1690171

Reaktionsgleichung

Reaktionsgleichung von HRID 1690171
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][OH: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]([CH:11]=[O:12])=[N:9][CH:10]=1)[CH3:1]

Komponenten

5

Edukt 3

HCID 6909Trichloroisocyanuric AcidHCID 2724126TempoHCID 66598374[5-(Propan-2-yloxy)pyridin-2-yl]methanol

Produkt 1

HCID 797940465-IsopropoxypicolinaldehydeAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

[5-(1-Methylethoxy)pyridin-2-yl]methanol (30 mg, 0.198 mmol) was dissolved in acetone (2.0 mL). The resultant mixture was added with 2,2,6,6-tetramethylpiperidine 1-oxyl (3.1 mg, 0.020 mmol) and trichloroisocyanuric acid (50 mg, 0.218 mmol) under ice-cold conditions, and stirred at 0° C. for 5 minutes. The reaction solution was concentrated in vacuo, added with 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 using silica-gel column chromatography (hexane/ethyl acetate), and 5-(1-methylethoxy)picolinaldehyde (25 mg, yield 85%) was obtained as a yellow oil.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additionadded with 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

Quellen und Nachweise

ORD-Eintrag
ord-d27e2569d0024a778adeb343fc81cafa
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153634B2

Verknüpfte Notizen

Wird geladen…