Khellinone → 1-(6-hydroxy-4,7-dimethoxy-2,3-dihydro-1-benzofuran-5-yl)ethanone

HRID 2248376Notes

Reaction equation

HRID 2248376 reaction equation
[C:1]([C:4]1[C:5]([OH:17])=[C:6]([O:15][CH3:16])[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[C:12]=1[O:13][CH3:14])(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([C:4]1[C:5]([OH:17])=[C:6]([O:15][CH3:16])[C:7]2[O:11][CH2:10][CH2:9][C:8]=2[C:12]=1[O:13][CH3:14])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 68086Khellinone

Product 1

HCID 2437691-(6-hydroxy-4,7-dimethoxy-2,3-dihydro-1-benzofuran-5-yl)ethanoneYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10 g of 5-acetyl-6-hydroxy-4,7-dimethoxybenzofuran in 100 ml of methanol are hydrogenated using 2 g of Pd/C (10%) at room temperature and under slightly superatmospheric pressure. When the absorption of hydrogen is complete, the mixture is filtered and the solvent is distilled off. 9.7 g of the desired product of melting point 100°-101° C. are obtained.

Workup

  1. customat room temperature
  2. customWhen the absorption of hydrogen
  3. filtrationthe mixture is filtered
  4. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-11488d71069e483089f9d718cff5c091
Source dataset
uspto-grants-1991_08
Patent number
US05039701

Reaction notes

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