Boron Trichloride → Kampferol-3,4'-dimethyl ether

HRID 377352Notes

Reaction equation

HRID 377352 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:29])[CH:14]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[O:16]2)=[C:11]([O:30]C)[CH:10]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.C([O-])(=O)C.[Na+]>C(Cl)Cl>[OH:30][C:11]1[CH:10]=[C:9]([OH:8])[CH:18]=[C:17]2[C:12]=1[C:13](=[O:29])[CH:14]=[C:15]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)[O:16]2

Participants

5

Reactant 3

HCID 25135Boron TrichlorideHCID 517045Sodium AcetateHCID 193585797-Benzyloxy-2-(3,4-dimethoxy-phenyl)-5-methoxy-chromen-4-one

Product 1

HCID 5351234Kampferol-3,4'-dimethyl etherYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-benzyloxy-3',4',5-trimethoxy flavone (565 mg, 1.35 mmol) was dissolved in 17 mL of methylenechloride, and then 1M of boron trichloride (3.79 mL, 3 equivalents) was added at temperature of 0° C. Then the reaction mixture was stirred for 30 minutes. When aqueous sodium acetate solution (5 mL) was added to the resultant reaction mixture, the product was obtained as a yellow crystal. The product was triturated with hexane and filtered to give the titled product (271 mg, 64%).

Workup

  1. customreaction mixture
  2. customthe product was obtained as a yellow crystal
  3. customThe product was triturated with hexane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-3c27b2358b4e4bbe8759bae99d3b12a1
Source dataset
uspto-grants-2000_02
Patent number
US06025387

Reaction notes

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