Sodium Iodide → HCID 54472244, compound

HRID 1978777Notes

Reaction equation

HRID 1978777 reaction equation
[OH:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH3:25]>CN(C=O)C.O>[CH2:23]([O:22][CH2:21][CH2:20][O:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 785157-BenzofuranolHCID 1235061-(2-Chloroethoxy)propane

Product 1

HCID 54472244HCID 54472244, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 7-hydroxybenzofuran (2.609) in DMF (70 ml) were added potassium carbonate (6.97 g) and sodium iodide (7.55 g) and then was added 2-chloroethylpropylether (4.76 g), and the mixture was stirred, under nitrogen atmosphere, at 95° C. for 3 days and cooled. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water (three times) and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography to give brown oil of 7-propoxyethoxybenzofuran (3.76 g).

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water (three times) and saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated
  6. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-87ae1f8a89a841c792f7a046bb54a659
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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