Iodine → HCID 86758968, compound

HRID 412865Notes

Reaction equation

HRID 412865 reaction equation
C([O:4][C@H:5]1[C@@H:38]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@@H:37]([CH2:47][O:48]CC=C)[O:36][C@@H:7]([O:8][CH2:9][CH:10]([CH2:12][CH2:13][CH2:14][C@H:15]([C@@H:17]2[C@:34]3([CH3:35])[C@H:20]([C@H:21]4[C@H:31]([CH2:32][CH2:33]3)[C@:29]3([CH3:30])[CH:24]([CH2:25][CH2:26][CH2:27][CH2:28]3)[CH2:23][CH2:22]4)[CH2:19][CH2:18]2)[CH3:16])[CH3:11])[C@@H:6]1[O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)C=C.II.O>O1CCCC1.C(Cl)(Cl)Cl.[Ir]>[CH2:53]([O:52][C@@H:6]1[C@@H:5]([OH:4])[C@@H:38]([O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C@@H:37]([CH2:47][OH:48])[O:36][C@H:7]1[O:8][CH2:9][CH:10]([CH2:12][CH2:13][CH2:14][C@H:15]([C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C@H:21]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[CH:24]([CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:23][CH2:22]3)[CH2:19][CH2:18]1)[CH3:16])[CH3:11])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

7

Reactant 3

HCID 807IodineHCID 962WaterHCID 131723894HCID 131723894, compound

Product 1

HCID 86758968HCID 86758968, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 23924IridiumCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Iridium complex (1,5-cyclooctadiene bis(methyldiphenylphosphine)iridium hexafluorophosphate, 136 mg, 0.12 mmol) was suspended in tetrahydrofuran (5 mL), and activated by stirring under H2 flow. To this solution Compound 25 (940 mg, 1.16 mmol) dissolved in tetrahydrofuran (5 mL) was added, and the mixture was stirred at room temperature for 1 hour under argon gas flow. Iodine (588 mg), water (30 mL) and tetrahydrofuran (15 mL) were added thereto, and the mixture was further stirred at room temperature for 1.5 hours. The reaction mixture was diluted with chloroform, and 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:acetone=6:1) to obtain Compound 26 (748 mg, 88.2%).

Workup

  1. additionwas added
  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 1.5 hours
  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:acetone=6:1)

Sources & evidence

ORD record
ord-bf2161dbd39d4271ab0b644508ca4b70
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

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