Iodine → 1-Iodomethyl-4-methyl-2-oxabicyclo[2.2.2]-octan-3-one

HRID 2225488Notes

Reaction equation

HRID 2225488 reaction equation
[I:1]I.[CH3:3][C:4]1([C:11]([OH:13])=[O:12])[CH2:9][CH2:8][C:7](=[CH2:10])[CH2:6][CH2:5]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[I:1][CH2:10][C:7]12[CH2:6][CH2:5][C:4]([CH3:3])([CH2:9][CH2:8]1)[C:11](=[O:13])[O:12]2

Participants

5

Reactant 3

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 19004549HCID 19004549, compound

Product 1

HCID 190045791-Iodomethyl-4-methyl-2-oxabicyclo[2.2.2]-octan-3-oneYield 46.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7.5 g of iodine was added to a solution of 1.3 g of 1-methyl-4-methylene-1-cyclohexanecarboxylic acid in 50 ml of acetonitrile. The solution was reacted for 3 hours at room temperature. After reaction, 100 ml of an aqueous solution of sodium thiosulfate was added to the reaction solution. The solution was extracted five times with 30 ml of ethyl acetate. The organic layer obtained was washed three times with aqueous sodium thiosulfate solution and two times with an aqueous sodium chloride solution, and was dried over magnesium sulfate. The solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 10 g of silica gel. From the fraction eluted with hexane and ethyl acetate=1:1, the solvent was removed in vacuo, yielding 1.1 g of 1-iodomethyl-4-methyl-2-oxabicyclo[2.2.2]octan-3-one as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 3 hours at room temperature
  2. additionwas added to the reaction solution
  3. extractionThe solution was extracted five times with 30 ml of ethyl acetate
  4. customThe organic layer obtained
  5. washwas washed three times with aqueous sodium thiosulfate solution and two times with an aqueous sodium chloride solution
  6. dry with materialwas dried over magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. customThe oily substance obtained
  9. washFrom the fraction eluted with hexane and ethyl acetate=1:1
  10. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2bcbda0f3c4449d296276e5ed01148d9
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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