Iodine → HCID 57287130, compound

HRID 963008Notes

Reaction equation

HRID 963008 reaction equation
[I:1]I.C[Si](C)(C)[CH:5]=[CH:6][C:7]1[C:8](=[O:14])[CH2:9][CH2:10][CH2:11][C:12]=1[CH3:13].ClCCl.[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1>[I:1][CH:5]=[CH:6][C:7]1[C:8](=[O:14])[CH2:9][CH2:10][CH2:11][C:12]=1[CH3:13]

Participants

6

Reactant 4

HCID 807IodineHCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 57304809HCID 57304809, compound2×

Product 1

HCID 57287130HCID 57287130, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Iodine (750 mg, 2.96 mmol) was dissolved in 10 mL of THF and the solution was added to a solution of 2-(2-(trimethylsilyl)ethenyl)-3-methyl-2-cyclohexen-1-one (Compound 3, 560 mg, 2.70 mmol) and dichloromethane (50 mL) at room temperature. The solution was stirred overnight, 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-bef0fa6d836e4dc4a1a40f70e5a56180
Source dataset
uspto-grants-1998_06
Patent number
US05760276

Reaction notes

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