Sodium Iodide → 5-Methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentan-1-one

HRID 2091241Notes

Reaction equation

HRID 2091241 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=2[C:12]=1[CH3:13])=[O:7].[I-].[Na+].[CH3:22][O-:23].[Na+]>CO>[CH3:22][O:23][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=2[C:12]=1[CH3:13])=[O:7]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 10942334Sodium MethoxideHCID 667781595-Chloro-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentan-1-one

Product 1

HCID 667785075-Methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentan-1-oneYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (20 mL) of 5-chloro-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentan-1-one (1.93 g) synthesized in Example A120(1) in methanol were added sodium iodide (1.54 g) and sodium methoxide (1.86 g), and the mixture was stirred overnight with heating under reflux, and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-20% ethyl acetate/hexane) to give the title object compound (797 mg, 42%) as a white solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (0-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f9be1e6dd686439cbc04936d078f3083
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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