Sodium Iodide → HCID 54243733, compound

HRID 1978772Notes

Reaction equation

HRID 1978772 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][O:8][C:4]=2[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[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][O:8][C:4]=2[CH:3]=1)[CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1235061-(2-Chloroethoxy)propaneHCID 1288446-Hydroxybenzofuran

Product 1

HCID 54243733HCID 54243733, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 6-hydroxybenzofuran (1.38 g) in DMF (40 ml) were added potassium carbonate (3.70 g) and sodium iodide (4.01 g) and then was added 2-chloroethylpropylether (2.52 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 was washed with 1N sodium hydroxide solution (4 times), water (three times) and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give yellow oil of 6-propoxyethoxybenzofuran (1.50 g).

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted with ethyl acetate (twice)
  3. washThe organic layer was washed with 1N sodium hydroxide solution (4 times), water (three times) and saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-b7a3b7ef94c44d7d818490a45eabacb5
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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