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

HRID 1877030

Reaction equation

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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-50fbee2a58334c82a1e915c88b931746
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309580B2

Linked notes

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