Iodine → HCID 53905125, compound

HRID 412861Notes

Reaction equation

HRID 412861 reaction equation
C([O:4][C@H:5]1[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:18]([CH2:28][O:29]CC=C)[O:17][C@@H:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C@@H:6]1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)C=C.II.O>O1CCCC1.C(Cl)(Cl)Cl.[Ir]>[CH2:34]([O:33][C@@H:6]1[C@@H:5]([OH:4])[C@@H:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@@H:18]([CH2:28][OH:29])[O:17][C@H:7]1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 3

HCID 807IodineHCID 962WaterHCID 54324136HCID 54324136, compound

Product 1

HCID 53905125HCID 53905125, compoundYield 84.8%

Reagents, catalysts & solvents 3

HCID 23924IridiumCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Iridium complex (1,5-cyclooctadiene bis(methyldiphenylphosphine)iridium hexafluorophosphate, 172 mg, 0.15 mmol) was suspended in tetrahydrofuran (5 mL), and activated by stirring under H2 flow. Compound 15 (811 mg, 1.47 mmol) dissolved in tetrahydrofuran (5 mL) was added to the solution, and the mixture was stirred at room temperature for 1 hour under argon gas flow. Iodine (745 mg), water (38 mL), and tetrahydrofuran (15 mL) were added thereto, and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was diluted with chloroform, and then washed successively with saturated sodium thiosulfate solution, saturated aqueous sodium hydrogencarbonate, and saturated brine. The chloroform layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (toluene:EtOAc=5:2) to obtain Compound 16 (589 mg, 82.1%). Rf: 0.35 (toluene:AcOEt=2:1)

Workup

  1. additionwas added to the solution
  2. stirringthe mixture was stirred at room temperature for 1 hour under argon gas flow
  3. stirringthe mixture was further stirred at room temperature for 1 hour
  4. washwashed successively with saturated sodium thiosulfate solution, saturated aqueous sodium hydrogencarbonate, and saturated brine
  5. dry with materialThe chloroform layer was dried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (toluene:EtOAc=5:2)

Sources & evidence

ORD record
ord-b5100642db154cfcbd5ebb1e4600b523
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

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