Trichloroisocyanuric Acid → 5-Isopropoxypicolinaldehyde

Temperatur

0 °C

[5-(1-Methylethoxy)pyridin-2-yl]methanol (30 mg, 0.198 mmol) was dissolved in acetone (2.0 mL), added 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 the mixture was stirred at 0° C. for 5 minutes. The reaction solution was concentrated in vacuo, and the reaction solution was 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 5-(1-methylethoxy)-picolinaldehyde (25 mg (yield 85%)) was obtained as a yellow oil.

1. concentrationThe reaction solution was concentrated in vacuo
2. additionthe reaction solution was added 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)

ORD-Eintrag

ord-0363204f580243599b7a98c0e406af05

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08551985B2