Sodium Iodide → HCID 54239663, compound

HRID 1978767Notes

Reaction equation

HRID 1978767 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=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[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1)[CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1235061-(2-Chloroethoxy)propaneHCID 11651159Benzofuran-5-ol

Product 1

HCID 54239663HCID 54239663, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 5-hydroxybenzofuran (1.90 g) in DMF (30 ml) were added potassium carbonate (5.09 g) and sodium iodide (5.52 g) and then was added 2-chloroethylpropylether (3.47 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 (twice). The organic layer washed with 1N sodium hydroxide solution, water 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 yellow oil of 5-propoxyethoxybenzofuran (1.22 g).

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted with ethyl acetate (twice)
  3. washThe organic layer washed with 1N sodium hydroxide solution, water 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-0f55ac0f69684483a77752d69c04610a
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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