Iodine → HCID 22414832, compound

HRID 1721426Notes

Reaction equation

HRID 1721426 reaction equation
II.[I-].[K+].[OH:5][C:6]1[C:14](C(C)C=CC)=[CH:13][C:12]([CH3:20])=[C:11]2[C:7]=1[C:8]([CH3:23])([CH3:22])[C:9](=[O:21])[NH:10]2.S([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[CH2:14]([CH:6]([C:14]1[C:6]([OH:5])=[C:7]2[C:11](=[C:12]([CH3:20])[CH:13]=1)[NH:10][C:9](=[O:21])[C:8]2([CH3:23])[CH3:22])[CH:7]=[CH2:8])[CH3:13]

Participants

6

Reactant 4

HCID 807IodineHCID 4875Potassium Iodide2×HCID 23665763Sodium BisulfiteHCID 54049941HCID 54049941, compound

Product 1

HCID 22414832HCID 22414832, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent4×

Procedure

287 mg (1.13 mmol) of iodine was dissolved in a 4:1 chloroform-methanol solvent. To the solution were added 191 mg of potassium iodide and 4:1 chloroform-methanol solvent, followed by stirring to homogenize. This potassium iodide solution in 4:1 chloroform-methanol was added to a 4:1 chloroform-methanol solution of 259 mg (1 mmol) of 2,3-dihydro-4-hydroxy-5-(1-methyl-2-butenyl)-3,3,7-trimethyl-1H-indol-2-one under an argon atmosphere, and the mixture was stirred for 15 hours at room temperature. After the addition of an aqueous solution of sodium hydrogen sulfite, the reaction mixture was extracted with chloroform. The extract was washed with 1N sodium hydroxide solution and water, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by separation thin layer chromatography (silica gel, 2:1 mixture of n-hexane and ethyl acetate) to obtain, as a low polarity component, 122 mg (yield 31.7%) of light yellow crystals of the title compound (a).

Workup

  1. stirringto homogenize
  2. stirringthe mixture was stirred for 15 hours at room temperature
  3. extractionthe reaction mixture was extracted with chloroform
  4. washThe extract was washed with 1N sodium hydroxide solution and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by separation thin layer chromatography (silica gel, 2:1 mixture of n-hexane and ethyl acetate)

Sources & evidence

ORD record
ord-9d4b83bf8e0b435aa63a45f0b12c642b
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

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