Water → 1-(Benzofuran-5-yl)ethanone

HRID 1870841Notes

Reaction equation

HRID 1870841 reaction equation
[O:1]1[C:5]2[CH:6]=CC(C#N)=[CH:9][C:4]=2[CH:3]=[CH:2]1.C[Mg]Br.[O:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.S(=O)(=O)(O)O.O>O1CCCC1>[O:15]1[C:19]2[CH:2]=[CH:3][C:4]([C:5](=[O:1])[CH3:6])=[CH:9][C:18]=2[CH:17]=[CH:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 27951841-Benzofuran-5-carbonitrileHCID 178420675HCID 178420675, compound

Product 1

HCID 186937521-(Benzofuran-5-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-benzofurancarbonitrile (Japanese Patent Unexamined Publication No. 9-124,631) (1.30 g) in tetrahydrofuran (5 ml) was added 0.87 M methyl magnesium bromide-tetrahydrofuran solution (21 ml), and the resulting mixture was heated under reflux for 4 hours under a nitrogen atmosphere. The reaction mixture was acidified with conc. sulfuric acid and water was added thereto, after which the resulting mixture was subjected to extraction with diethyl ether. The extract solution was washed with water, dried and then distilled under reduced pressure to remove the solvent. The residue was purified by a silica gel column chromatography to obtain 1-benzofuran-5-yl-ethanone (1.21 g).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 4 hours under a nitrogen atmosphere
  3. additionwas added
  4. extractionafter which the resulting mixture was subjected to extraction with diethyl ether
  5. washThe extract solution was washed with water
  6. customdried
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-fb60d5576a794378a0cc24453be57489
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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