Water → HCID 70406248, compound

HRID 1284474Notes

Reaction equation

HRID 1284474 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.[C:12]1(/[C:18](/[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[I-:32].[Na+].O>CC(C)=O>[I:32][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]/[CH:19]=[C:18](\[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)/[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6101p-Toluenesulfonic acidHCID 13417327HCID 13417327, compound

Product 1

HCID 70406248HCID 70406248, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

p-Toluenesulfonate of (E)-7-phenyl-7-(3-pyridyl)-6-hepten-1-ol (15 g, 36 mmoles) and sodium iodide (18 g, 120 mmoles) were dissolved in acetone (100 ml) and the solution was stirred at room temperature for 3 hours. Water (200 ml) was added to the mixture and the product was extracted twice with ethyl ether. The organic layer was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure to give (E)-1-iodo-7-phenyl-7-(3-pyridyl)-6-heptene (13 g, 96%) as an oil.

Workup

  1. extractionthe product was extracted twice with ethyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e5b9c5ae02e4fc3af7f5c7663ad71e9
Source dataset
uspto-grants-1986_01
Patent number
US04563446

Reaction notes

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