Sodium Iodide → (E)-6,10-Dimethyl-5,9-undecadien-1-yl iodide

HRID 466640Notes

Reaction equation

HRID 466640 reaction equation
[CH3:1]/[C:2](/[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])=[CH:3]\[CH2:4][CH2:5][CH2:6][CH2:7]O.C(N(CC)CC)C.CS(Cl)(=O)=O.S([O-])(=O)(=O)C.[Na+].[I-:33]>C(Cl)Cl.CC(C)=O.CCOCC>[CH3:1]/[C:2](/[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])=[CH:3]\[CH2:4][CH2:5][CH2:6][CH2:7][I:33]

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 21631159(E)-6,10-dimethyl-5,9-undecadien-1-ol

Product 1

HCID 19927574(E)-6,10-Dimethyl-5,9-undecadien-1-yl iodideYield 85%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.80 g (9.20 mmol) of Part A (E)-6,10-dimethyl-5,9-undecadien-1-ol in 50 mL of methylene chloride and 2.00 mL (14.3 mmol) of triethylamine at 0° C. was treated with 1.14 g (10.00 mmol) of methanesulfonyl chloride dropwise over 0.2 hours. The reaction mixture was stirred for 1.0 hour when it was quenched with saturated aqueous NH4Cl solution and diluted with ether. The organic fraction was washed with saturated NaHCO3, brine, dried (Na2SO4) and evaporated to provide a crude colorless oil. The crude mesylate (~9.0 mmol) was diluted with 50 mL of acetone and treated with 4.05 g (27.00 mmol) of NaI, refluxed for 5 hours, and cooled to room temperature. The mixture was diluted with 250 mL of ether and extracted with NaHS03, brine, dried (MgSO4) and concentrated to provide a pale yellow oil. The oil was purified by flash chromatography (180 g of silica gel) eluting with hexane to provide 2.60 g (85%) of title iodide as a colorless oil.

Workup

  1. customwas quenched with saturated aqueous NH4Cl solution
  2. additiondiluted with ether
  3. washThe organic fraction was washed with saturated NaHCO3, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto provide a crude colorless oil
  7. temperaturerefluxed for 5 hours
  8. extractionextracted with NaHS03, brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customto provide a pale yellow oil
  12. customThe oil was purified by flash chromatography (180 g of silica gel)
  13. washeluting with hexane

Sources & evidence

ORD record
ord-3d0bfac3b9d54dcbbc4be59697bdca8a
Source dataset
uspto-grants-1992_10
Patent number
US05157027

Reaction notes

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