Water → 7-Propoxybenzofuran

HRID 1978776Notes

Reaction equation

HRID 1978776 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+].Br[CH2:18][CH2:19][CH3:20].O>CN(C=O)C>[CH2:18]([O:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 785157-Benzofuranol

Product 1

HCID 219957187-PropoxybenzofuranYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-hydroxybenzofuran (2.60 g) in DMF (30 ml) was added potassium carbonate (3.75 g) and then was added dropwise bromopropane (2.87 g) under nitrogen atmosphere, and the mixture was stirred overnight. 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 to give brown oil of 7-propoxybenzofuran (2.73 g).

Workup

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

Sources & evidence

ORD record
ord-b87799f1e0da47749420029525a5170c
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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