Iodine → HCID 86752693, compound

HRID 963013Notes

Reaction equation

HRID 963013 reaction equation
[I:1]I.C[Si](C)(C)[CH:5]=[CH:6][C:7]1[C:8](=[O:15])[CH2:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH:12]=1.C[Si](C)(C)/C=C/C1C(=O)CCC(C)(C)C=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1.ClCCl>[I:1]/[CH:5]=[CH:6]/[C:7]1[C:8](=[O:15])[CH2:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH:12]=1

Participants

7

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 18913646HCID 18913646, compoundHCID 54526213HCID 54526213, compound

Product 1

HCID 86752693HCID 86752693, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Iodine (657 mg, 2.59 mmol) was dissolved in 5 mL of THF and the solution was added to a solution of 2-(2-(trimethylsilyl)ethenyl)-4,4-dimethyl-2-cyclohexen-1-one (Compound 18, 575 mg, 2.59 mmol) and dichloromethane (15 mL) at room temperature. The solution was stirred for 6 hours, and then treated with 10% aqueous Na2S2O3 to remove the excess iodine. The layers were separated and the aqueous layer was extracted 3× with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel (9:1, hexane:ethyl acetate) to give the product as a brown oil.

Workup

  1. customto remove the excess iodine
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted 3× with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (9:1, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-027b5ce0c81a4eb8a5a8e15eaf16bbbd
Source dataset
uspto-grants-1998_06
Patent number
US05760276

Reaction notes

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