Triacetoxyperiodinane → 2-Methyl-5-phenyl-3-furaldehyde

HRID 1877030

Reaktionsgleichung

Reaktionsgleichung von HRID 1877030
CC(OI1(OC(C)=O)(OC(C)=O)[O:14][C:12](=O)[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)=O>O>[CH3:7][C:6]1[O:14][C:12]([C:11]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[CH:10][C:11]=1[CH:12]=[O:14]

Komponenten

3

Edukt 1

HCID 159087Triacetoxyperiodinane

Produkt 1

HCID 27953132-Methyl-5-phenyl-3-furaldehydeAusbeute 129,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (2-methyl-5-phenylfuran-3-yl)methanol (4.7 g) obtained by the above-mentioned reaction in methylene chloride (30 mL) was added a Dess-Martin reagent (12.7 g) at 0° C., and the mixture was stirred at 0° C. for 2 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 20% ethyl acetate/hexane) to give the title compound (3.6 g, 78%) as a yellow crystal.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-50fbee2a58334c82a1e915c88b931746
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309580B2

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