Sodium Iodide → 1-iodo-7-(bicyclo[3.2.1]oct-2-yl)-1-E-hepten-3-one

HRID 26307Notes

Reaction equation

HRID 26307 reaction equation
Cl/[CH:2]=[CH:3]/[C:4](=[O:17])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:15][CH2:14][CH:13]2[CH2:16][CH:10]1[CH2:11][CH2:12]2.[I-:18].[Na+]>CC(C)=O>[I:18]/[CH:2]=[CH:3]/[C:4](=[O:17])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:15][CH2:14][CH:13]2[CH2:16][CH:10]1[CH2:11][CH2:12]2

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 21325429HCID 21325429, compound

Product 1

HCID 213254401-iodo-7-(bicyclo[3.2.1]oct-2-yl)-1-E-hepten-3-oneYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3.2 g (13 mmol) of 1-chloro-7-(bicyclo-[3.2.1]oct-2-yl)-1E-hepten-3-one and 7.5 g (50 mmol) of sodium iodide in 25 ml of dry acetone (distilled from potassium carbonate) was refluxed for 18 hr under nitrogen. The solvent was removed in vacuo, and the residue was taken up in 50 ml of water and then extracted three times with 30 ml portions of ether. The combined ether extracts were washed with aqueous sodium thiosulfate, dried (MgSO4) and evaporated in vacuo to yield 3.8 g (88%) of 1-iodo-7-(bicyclo[3.2.1]oct-2-yl)-1-E-hepten-3-one.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionextracted three times with 30 ml portions of ether
  3. washThe combined ether extracts were washed with aqueous sodium thiosulfate
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-65e3ecf792784c20b62b29e6c0afa920
Source dataset
uspto-grants-1979_04
Patent number
US04149017

Reaction notes

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