Iodine → HCID 14332264, compound

HRID 412854Notes

Reaction equation

HRID 412854 reaction equation
C([O:4][C@H:5]1[C@@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:17]([CH2:27][O:28]CC=C)[O:16][C@@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@@H:6]1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)C=C.O.II>O1CCCC1.C(OCC)(=O)C.[Ir]>[CH2:33]([O:32][C@@H:6]1[C@@H:5]([OH:4])[C@@H:18]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@@H:17]([CH2:27][OH:28])[O:16][C@H:7]1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 3

HCID 807IodineHCID 962WaterHCID 54511176HCID 54511176, compound

Product 1

HCID 14332264HCID 14332264, compoundYield 98.4%

Reagents, catalysts & solvents 3

HCID 23924IridiumCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under hydrogen gas atmosphere, a solution of Compound 12 (8.9 g, 16.7 mmol) in tetrahydrofuran (80 ml) was added to a solution of activated iridium complex (Ir(CoD)(PMePh2)2PF6, 287 mg, 0.34 mmol) in tetrahydrofuran (60 ml) at room temperature, and the mixture was stirred for 7 hours. Subsequently, water (100 ml) and iodine (8.5 g, 67.1 mmol) were added to the reaction mixture, and it was stirred for 15 hours. The reaction mixture was diluted with ethyl acetate, washed successively with saturated sodium thiosulfate solution, saturated aqueous sodium hydrogencarbonate, and saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was recrystallized (ethanol/dichloromethane/diethyl ether) to obtain Compound 13 (7.4 g, 97%).

Workup

  1. stirringwas stirred for 15 hours
  2. washwashed successively with saturated sodium thiosulfate solution, saturated aqueous sodium hydrogencarbonate, and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was recrystallized (ethanol/dichloromethane/diethyl ether)

Sources & evidence

ORD record
ord-ad0d000222034b759c68517f83dfd098
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

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