Sodium Iodide → HCID 10871691, compound

HRID 488159Notes

Reaction equation

HRID 488159 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6]/[CH:7]=[C:8](\[CH3:20])/[CH2:9][CH2:10]/[CH:11]=[C:12](\[CH3:19])/[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])(=O)=O.[I-:28].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O>[CH3:20]/[C:8](/[CH2:9][CH2:10]/[CH:11]=[C:12](\[CH3:19])/[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:7]\[CH2:6][CH2:5][I:28]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 10548453HCID 10548453, compound

Product 1

HCID 10871691HCID 10871691, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The (E,E)-4,8,12-trimethyl-3,7,11-tridecatrienyl tosylate obtained from previous step was dissolved in acetone (50 mL), then added sodium iodide (3.30 g, 22 mmol) and the resulting mixture was stirred at room temperature for 0.5 hours followed by heating at reflux for 3 hours. After cooling, the reaction mixture was poured into cold aqueous sodium thiosulfate solution and extracted with ether. The ethereal extract was washed with water, dried and filtered. Evaporation of the filtrate left a residue which was purified by flash chromatography on a silica gel column. Elution of the column with Hexane:ether (50:1, v:v) provided the title compound (1.85 g, 5.34 mmol, 76% for two steps) as a colorless oil.

Workup

  1. temperatureby heating
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. extractionextracted with ether
  5. extractionThe ethereal extract
  6. washwas washed with water
  7. customdried
  8. filtrationfiltered
  9. customEvaporation of the filtrate
  10. waitleft a residue which
  11. customwas purified by flash chromatography on a silica gel column
  12. washElution of the column with Hexane:ether (50:1, v:v)

Sources & evidence

ORD record
ord-0c3bddd274e846acaecc68d80b047642
Source dataset
uspto-grants-1994_03
Patent number
US05298655

Reaction notes

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