Isopropyl iodide → HCID 21713937, compound

HRID 618003Notes

Reaction equation

HRID 618003 reaction equation
[Mg].[CH:2](I)([CH3:4])[CH3:3].CO[C:8]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11]>C(OCC)C>[CH:2]([C:8]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 218622,3-DimethoxybenzonitrileHCID 5462224Magnesium2×

Product 1

HCID 21713937HCID 21713937, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 2.76 g (0.115 mol) of magnesium in 75 mL of diethylether, was slowly added 24.31 g (0.143 mol) isopropyl iodide. The resulting reaction mixture was allowed to react until all of the magnesium was consumed. Then, a solution of 15.0 g (0.92 mol) of 2,3-dimethoxy benzonitrile in 75 mL of diethylether was added over ninety minutes. The resulting reaction mixture was reacted overnight at room temperature and then refluxed for four hours. The resultant reaction mixture was then cooled to 0° C., and the top layer was decanted into saturated ammonium chloride and ice. The resultant layers were separated and the organic layer was washed sequentially with a dilute sodium hydroxide solution, water, and a dilute hydrochloric acid solution, dried over sodium sulfate, filtered and then concentrated to provide an orange oil. This oil was distilled under reduced pressure (5 inch vigreux column; 0.2 mm Hg) to provide 6.25 g of an orange oil.

Workup

  1. customThe resulting reaction mixture
  2. customwas consumed
  3. customThe resulting reaction mixture
  4. customwas reacted overnight at room temperature
  5. temperaturerefluxed for four hours
  6. customThe resultant reaction mixture
  7. customthe top layer was decanted into saturated ammonium chloride and ice
  8. customThe resultant layers were separated
  9. washthe organic layer was washed sequentially with a dilute sodium hydroxide solution, water
  10. dry with materiala dilute hydrochloric acid solution, dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto provide an orange oil
  14. distillationThis oil was distilled under reduced pressure (5 inch vigreux column; 0.2 mm Hg)

Sources & evidence

ORD record
ord-e9bdca144c944dc880ac4400fe43c006
Source dataset
uspto-grants-1999_09
Patent number
US05952343

Reaction notes

Loading…