3-(4-Methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl acetate → HCID 9926870, compound

HRID 603275Notes

Reaction equation

HRID 603275 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:23])[C:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:11][O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([OH:23])[CH:10]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[CH2:11][O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 9088273-(4-Methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl acetate

Product 1

HCID 9926870HCID 9926870, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium-on-charcoal (5%, 0.08 g) was added to a suspension of 7-acetoxy-4′-methoxyisoflavone (0.5 g, 1.6 mmol) in absolute ethanol (400 ml) and the mixture was stirred at room temperature under a hydrogen atmosphere for 55 hours. The catalyst was removed by filtration through Celite and the filtrate was evaporated in vacuo to yield 7-acetoxy-4′-methoxyisoflavan-4-ol (0.51 g, 100%) in quantitative yield. A nuclear magnetic resonance spectrum revealed the product to be a clean 1:1 mixture of cis- and trans-7-acetoxy-4′-methoxyisoflavan-4-ol.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-ae4581d882744155a243e4fa46ad46ea
Source dataset
uspto-grants-2011_03
Patent number
US07906660B2

Reaction notes

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