HCID 9799644, compound → HCID 9842545, compound

HRID 1724614Notes

Reaction equation

HRID 1724614 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13](=[O:15])[CH3:14])[O:8][CH:7]=[C:6]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=1)[C:5]2=[O:26]>O=[Pt]=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13](=[O:15])[CH3:14])[O:8][CH2:7][CH:6]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=1)[C:5]2=[O:26]

Participants

4

Reactant 1

HCID 9799644HCID 9799644, compound

Product 1

HCID 9842545HCID 9842545, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Adam's catalyst (0.045 g) was added to a solution of 6-chloro-4′,7-diacetoxyisoflavone (0.25 g, 0.7 mmol) in ethyl acetate (30 ml) and the mixture was stirred at room temperature under a hydrogen atmosphere for 24 h. The catalyst was removed by filtration through Celite and the resulting filtrate was evaporated in vacuo. The residue was recrystallised from ethanol to yield 6-chloro-4′,7-diacetoxyisoflavan4-one (0.15 g, 60%) as colourless plates. 1H NMR (CDCl3): δ 2.29 (s, 3H, OCOCH3), 2.37 (s, 3H, OCOCH3), 3.98 (dd, 1H, J 6.0 Hz, 7.5 Hz, H3), 4.68 (m, 2H, H2), 6.87 (s, 1H, H8), 7.07 (d, 2H, J 8.6 Hz, ArH), 7.27 (d, 2H, J 8.6 Hz, ArH), 8.01 (s, 1H, H5).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customthe resulting filtrate was evaporated in vacuo
  3. customThe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-743c4d709fcf4a8a9cf9cb7d9e9f23d0
Source dataset
uspto-grants-2009_02
Patent number
US07488494B2

Reaction notes

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