Sodium Iodide → HCID 19966123, compound

HRID 977863Notes

Reaction equation

HRID 977863 reaction equation
[I-:1].[Na+].[C:3]1([C:9]2([CH2:14]CS([O-])(=O)=O)[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(C(C)=O)C(C)C>[C:3]1([C:9]2([CH2:14][I:1])[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 19966158HCID 19966158, compound

Product 1

HCID 19966123HCID 19966123, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

5.00 g (33.3 mmol) of sodium iodide were added to a solution of 1.00 g (3.93 mmol) of (1-phenylcyclopentyl)methylmethanesulfonate [prepared as described in step (ii) above] in 10 ml of methyl isobutyl ketone, and the resulting mixture was heated under reflux for 18 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was partitioned between diethyl ether and water. The organic phase was washed with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 50 g of silica gel, using a 1:1 by volume mixture of methylene chloride and hexane as the eluent, to give 504 mg (yield 45%) of the title compound as an oil.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. customthe resulting residue was partitioned between diethyl ether and water
  5. washThe organic phase was washed with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe resulting residue was purified by column chromatography through 50 g of silica gel
  9. additionby volume mixture of methylene chloride and hexane as the eluent

Sources & evidence

ORD record
ord-cdeff841334b42cc8fdd3db3999394eb
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

Loading…