Water → 7-Propoxybenzofuran

HRID 1978771Notes

Reaction equation

HRID 1978771 reaction equation
O[C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][O:8][C:4]=2[CH:3]=1.[C:11](=[O:14])([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19]C.O>CN(C=O)C>[CH2:11]([O:14][C:3]1[C:4]2[O:8][CH:7]=[CH:6][C:5]=2[CH:9]=[CH:10][CH:2]=1)[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 1288446-Hydroxybenzofuran

Product 1

HCID 219957187-PropoxybenzofuranYield 54.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-hydroxybenzofuran (1.30 g) in DMF (15 ml) was added potassium carbonate (1.88 g) and then was added dropwise bromopropane (1.44 g) under nitrogen atmosphere, and the mixture was refluxed overnight. To the mixture was added water, and the mixture was extracted with ethyl acetate (twice). The organic layer was washed with water (three times) and then washed with saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give yellow oil of 7-propoxybenzofuran (0.93 g).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. extractionthe mixture was extracted with ethyl acetate (twice)
  3. washThe organic layer was washed with water (three times)
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-c8792cddfd2842e5819d449e2b0c73f7
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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