HCID 9884853, compound → HCID 9819969, compound

HRID 1724617Notes

Reaction equation

HRID 1724617 reaction equation
[C:1]([O:4][C:5]1[CH:26]=[CH:25][C:8]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][C:14]([O:21][C:22](=[O:24])[CH3:23])=[CH:15][C:16]=3[CH3:20])[O:11][CH:10]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:4][C:5]1[CH:26]=[CH:25][C:8]([CH:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][C:14]([O:21][C:22](=[O:24])[CH3:23])=[CH:15][C:16]=3[CH3:20])[O:11][CH2:10]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 9884853HCID 9884853, compound

Product 1

HCID 9819969HCID 9819969, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on barium sulfate (5%, 0.06 g) was added to a solution of 4′,7-diacetoxy-5-methylisoflavone (0.30 g, 0.8 mmol) in ethyl acetate (50 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 4′,7-diacetoxy-5-methylisoflavan-4-one (0.20 g, 67%) as colourless plates. m.p. 143-45° C., 1H NMR (CDCl3): δ 2.29 (s, 3H, OCOCH3), 2.30 (s, 3H, OCOCH3), 2.62 (s, 3H, Me), 3.95 (t, 1H, J 7.2 Hz, H3), 4.62 (d, 2H, J 6.8 Hz, H2), 6.59 (d, 1H, J 2.2 Hz, H8), 6.66 (d, 1H, J 2.2 Hz, H5), 7.07 (d, 2H, J 8.3 Hz, ArH), 7.28 (d, 2H, J 8.3 Hz, ArH).

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-edb8ec63d47f475b8708e21cbbd65125
Source dataset
uspto-grants-2009_02
Patent number
US07488494B2

Reaction notes

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