Water → 1-Benzofuran-5-carbaldehyde

HRID 2080153Notes

Reaction equation

HRID 2080153 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.O>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 7359012,3-Dihydrobenzofuran-5-carboxaldehyde

Product 1

HCID 27738751-Benzofuran-5-carbaldehydeYield 21%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2,3-dihydro-benzofuran-5-carbaldehyde described in Preparation Example 174 (6.00 g, 40.5 mmol) in toluene (120 mL) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (18.3 g, 81 mmol), and the solution was refluxed for 4 hours 30 minutes. The reaction solution was cooled to room temperature, water was added, the solution was extracted with ethyl acetate and tetrahydrofuran, and the organic layer was washed with brine. Anhydrous magnesium sulfate was added to the organic layer for drying, which was then filtered, the filtrate was concentrated in vacuo, the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1), and the title compound (1.24 g, 21%) was obtained as a pale yellow oil.

Workup

  1. temperaturethe solution was refluxed for 4 hours 30 minutes
  2. extractionthe solution was extracted with ethyl acetate and tetrahydrofuran
  3. washthe organic layer was washed with brine
  4. additionAnhydrous magnesium sulfate was added to the organic layer
  5. customfor drying
  6. filtrationwhich was then filtered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-1293cfc40ced42f5acdedabddc778f7a
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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