Iodine → HCID 131723887, compound

HRID 412859Notes

Reaction equation

HRID 412859 reaction equation
C([O:4][C@H:5]1[C@@H:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:9]([CH2:19][O:20]CC=C)[O:8][C@@H:7]([O:24][CH2:25][C@H:26]([CH2:42][O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C@@H:6]1[O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)C=C.II.O>O1CCCC1.C(Cl)(Cl)Cl.[Ir]>[CH2:59]([O:58][C@@H:6]1[C@@H:5]([OH:4])[C@@H:10]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C@@H:9]([CH2:19][OH:20])[O:8][C@H:7]1[O:24][CH2:25][C@H:26]([CH2:42][O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

7

Reactant 3

HCID 807IodineHCID 962WaterHCID 131723888HCID 131723888, compound

Product 1

HCID 131723887HCID 131723887, compoundYield 87.4%

Reagents, catalysts & solvents 3

HCID 23924IridiumCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Iridium complex (1,5-cyclooctadiene bis(methyldiphenylphosphine)iridium hexafluorophosphate, 112 mg, 0.096 mmol) was suspended in tetrahydrofuran (5 mL), and activated by stirring under H2 flow. To this solution, Compound 5 (864 mg, 0.95 mmol) dissolved in tetrahydrofuran (5 mL) was added, and the mixture was stirred at room temperature for 2 hours under argon gas flow. Then, iodine (484 mg), water (24.7 mL) and tetrahydrofuran (15 mL) were added thereto, and the mixture was further stirred at room temperature for 2 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:EtOAc=5:2) to obtain Compound 6 (686.6 mg, 87.1%).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 2 hours under argon gas flow
  3. stirringthe mixture was further stirred at room temperature for 2 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:EtOAc=5:2)

Sources & evidence

ORD record
ord-6cafa2a4157340ae9f2c3ee3d401517b
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

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