Pyridine → 2-(4-Ethylphenyl)-1-benzofuran

HRID 1577033Notes

Reaction equation

HRID 1577033 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].N1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:11]([C:12]1[CH:4]=[CH:3][C:2]([C:7]2[O:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH:6]=2)=[CH:14][CH:13]=1)[CH3:10]

Participants

3

Reactant 2

HCID 1049PyridineHCID 107842-Iodophenol

Product 1

HCID 227689002-(4-Ethylphenyl)-1-benzofuran

Procedure

A flask containing 5.4 g. (0.028 mol.) of cuprous 4-ethylphenylacetylide in 100 ml. of pyridine is thoroughly flushed with nitrogen. A solution of 6.19 g. (0.028 mol.) of o-iodophenol in 50 ml. of pyridine is added under nitrogen and the reaction mixture is stirred and heated at 120° for 22 hours. The pyridine is removed by distillation in vacuo, the residue is added to an ice-water mixture and the gummy precipitate is collected and dissolved in methylene chloride. The methylene chloride solution is washed with 3N hydrochloric acid and water and concentrated under reduced pressure to give a residue which is chromatographed on a silica gel "dry-column" to give 2-(4-ethylphenyl)benzofuran.

Workup

  1. additionA flask containing 5.4 g
  2. customof pyridine is thoroughly flushed with nitrogen
  3. temperatureheated at 120° for 22 hours
  4. customThe pyridine is removed by distillation in vacuo
  5. additionthe residue is added to an ice-water mixture
  6. customthe gummy precipitate is collected
  7. dissolutiondissolved in methylene chloride
  8. washThe methylene chloride solution is washed with 3N hydrochloric acid and water
  9. concentrationconcentrated under reduced pressure
  10. customto give a residue which
  11. customis chromatographed on a silica gel "dry-column"

Sources & evidence

ORD record
ord-61fad645a9f44f32b78227f61df6cb6a
Source dataset
uspto-grants-1976_09
Patent number
US03983245

Reaction notes

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