isoformononetin → HCID 44227176, compound

HRID 1436311Notes

Reaction equation

HRID 1436311 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[CH:14][CH:15]=3)[O:10][CH:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl.C(#N)C>O>[CH3:20][O:19][C:13]1[CH:12]=[C:11]2[C:16]([C:17](=[O:18])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([O:1][CH2:27][CH:29]4[CH2:30][O:31]4)=[CH:7][CH:6]=3)=[CH:9][O:10]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 3764isoformononetinHCID 6342AcetonitrileHCID 7835EpichlorohydrinHCID 11430Potassium Carbonate

Product 1

HCID 44227176HCID 44227176, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-methoxy-4′-hydroxyisoflavone (1, 0.27 g, 1 mmol), K2CO3 (0.41 g, 3 mmol), epichlorohydrin (0.3 g, 3 mmol) and acetonitrile (30 mL) was refluxed with stirring for 4 hrs (TLC monitoring). The mixture was evaporated in vacuo to give a residue which was treated with H2O (50 mL). The precipitate thus formed was collected, purified by column chromatography (MeOH/CH2Cl2=1:50), and crystallized from EtOH to give the title compound 3 (0.14 g, 43% yield). M.p.: 153-154° C.

Workup

  1. temperaturewas refluxed
  2. customThe mixture was evaporated in vacuo
  3. customto give a residue which
  4. customThe precipitate thus formed
  5. customwas collected
  6. custompurified by column chromatography (MeOH/CH2Cl2=1:50)
  7. customcrystallized from EtOH

Sources & evidence

ORD record
ord-a0d954a3b1b14517973cd9c0704fbc69
Source dataset
uspto-grants-2009_11
Patent number
US07618998B2

Reaction notes

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