HCID 18505670, compound → HCID 18505823, compound

HRID 1357208Notes

Reaction equation

HRID 1357208 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[C:19]([O:21]CC4C=CC=CC=4)[CH:18]=[CH:17][C:15]=3[CH:16]=2)[O:8][C:7](=[O:29])[C:6]=1[CH3:30])(=[O:3])[CH3:2]>CCO.O1CCOCC1.[Pd]>[C:1]([O:4][C:5]1[C:10]([CH3:11])=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:15]=3[CH:16]=2)[O:8][C:7](=[O:29])[C:6]=1[CH3:30])(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 18505670HCID 18505670, compound

Product 1

HCID 18505823HCID 18505823, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-acetyloxy-6-(6-(benzyloxy)benzofuran-2-yl)-3,5-dimethyl-2H-pyran-2-one (500 mg) in EtOH (50 ml) and 1,4-dioxane (50 ml) there was added 10% Pd/C (100 mg), and the mixture was vigorously stirred at room temperature for 3 hours under a hydrogen gas atmosphere. The reaction solution was celite filtered, and then the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1) to obtain 4-acetyloxy-3,5-dimethyl-6-(6-hydroxybenzofuran-2-yl)-2H-pyran-2-one.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1)

Sources & evidence

ORD record
ord-05f141f3d609455eb2370d294118e227
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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