HCID 9819870, compound → HCID 9928623, compound

HRID 603277Notes

Reaction equation

HRID 603277 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](=[C:13]([CH3:24])[C:14]([O:20][C:21](=[O:23])[CH3:22])=[CH:15][CH:16]=3)[O:11][CH:10]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([O:4][C:5]1[CH:26]=[CH:25][C:8]([CH:9]2[CH:18]([OH:19])[C:17]3[C:12](=[C:13]([CH3:24])[C:14]([O:20][C:21](=[O:23])[CH3:22])=[CH:15][CH:16]=3)[O:11][CH2:10]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 9819870HCID 9819870, compound

Product 1

HCID 9928623HCID 9928623, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium-on-charcoal (5%, 0.12 g) was added to a suspension of 4′,7-diacetoxy-8-methylisoflavone (1.0 g, 2.8 mmol) in methanol (200 ml) and the mixture was stirred at room temperature under a hydrogen atmosphere for 55 h. The catalyst was removed by filtration through Celite and the filtrate was evaporated in vacuo to yield 4′,7-diacetoxy-8-methylisoflavan-4-ol in quantitative yield, m.p. 135-37° C. A nuclear magnetic resonance spectrum revealed the product to be a clean 1:1 mixture of cis- and trans-4′,7-diacetoxy-8-methylisoflavan-4-ol. Mass spectrum: 356 (M, 53%); 254 (86); 253 (100); 240 (80); 196 (37).

Workup

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

Sources & evidence

ORD record
ord-8c120a0579e1404fb6d1b73a1a45d0d6
Source dataset
uspto-grants-2011_03
Patent number
US07906660B2

Reaction notes

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