Methyl iodide → 7-Benzyloxy-3-(4-chlorophenyl)-2-isopropyl-8-methoxy-chromen-4-one

HRID 14465Notes

Reaction equation

HRID 14465 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([OH:19])=[C:17]2[C:12]([C:13](=[O:30])[C:14]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[C:15]([CH:20]([CH3:22])[CH3:21])[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.IC.[C:33]([O-])([O-])=O.[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:33])=[C:17]2[C:12]([C:13](=[O:30])[C:14]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[C:15]([CH:20]([CH3:22])[CH3:21])[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 687027787-Benzyloxy-3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-chromen-4-one

Product 1

HCID 687032587-Benzyloxy-3-(4-chlorophenyl)-2-isopropyl-8-methoxy-chromen-4-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-benzyloxy-3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-chromen-4-one (3.01 g, 7.15 mmol) and iodomethane (1.17 g, 8.22 mmol) in N,N-dimethylformamide (60 ml) is added K2CO3 (1.98 g, 14.3 mmol). The reaction mixture is stirred at room temperature for 72 h. The mixture is diluted with ethyl acetate and water, and the organic phase is washed with sodium thiosulfate solution and brine, dried (MgSO4) and concentrated in vacuo. The resulting off-white solid residue is triturated with ethyl acetate to afford the title compound as a white solid.

Workup

  1. washthe organic phase is washed with sodium thiosulfate solution and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting off-white solid residue is triturated with ethyl acetate

Sources & evidence

ORD record
ord-e8fed43ffcc74153aae0b172cb781dc4
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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