Acetonitrile → 3-(3,4-Dimethoxyphenyl)-7-(oxiran-2-ylmethoxy)-4H-chromen-4-one

HRID 1436312Notes

Reaction equation

HRID 1436312 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:29]([CH:31]1[O:33][CH2:32]1)Cl.C(#N)C>O>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([C:7]2[C:6](=[O:22])[C:5]3[C:10](=[CH:11][C:2]([O:1][CH2:29][CH:31]4[CH2:32][O:33]4)=[CH:3][CH:4]=3)[O:9][CH:8]=2)[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 5748605Cladrin

Product 1

HCID 442271773-(3,4-Dimethoxyphenyl)-7-(oxiran-2-ylmethoxy)-4H-chromen-4-oneYield 70.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-hydroxy-3′,4′-dimethoxyisoflavone (2, 0.30 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=1:100), and crystallized from EtOH to give the title compound 4 (0.25 g, 70% yield). M.p.: 161-162° 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=1:100)
  7. customcrystallized from EtOH

Sources & evidence

ORD record
ord-f74a14159f7446b78a33b862a4af58fa
Source dataset
uspto-grants-2009_11
Patent number
US07618998B2

Reaction notes

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