Triacetoxyperiodinane → HCID 83598147, compound

HRID 1877106Notes

Reaction equation

HRID 1877106 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>[CH2:7]([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])[CH3:8]

Participants

3

Reactant 1

HCID 159087Triacetoxyperiodinane

Product 1

HCID 83598147HCID 83598147, compoundYield 137.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2-ethyl-5-phenylfuran-3-yl)methanol (5.9 g) obtained by the above-mentioned reaction in methylene chloride (30 mL) was added Dess-Martin reagent (14.8 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 25% ethyl acetate/hexane) to give the title compound (4.8 g, 83%) as an oil.

Workup

  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 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-be8812ff66404788b49dc71de034a884
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

Loading…