Sodium periodate → HCID 67517034, compound

HRID 2173176Notes

Reaction equation

HRID 2173176 reaction equation
[CH3:1][C:2](=C)[CH2:3][C:4]1[CH:13]=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1.I([O-])(=O)(=O)=[O:16].[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[O:16]=[C:2]([CH3:1])[CH2:3][C:4]1[CH:13]=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 67517295HCID 67517295, compound

Product 1

HCID 67517034HCID 67517034, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(2-methylprop-2-en-1-yl)-2-benzofuran-1(3H)-one (175 mg, 0.930 mmol) in THF was added osmium tetroxide (295 mg, 0.0460 mmol) and the mixture was stirred for 10 minutes. Then a solution of sodium periodate (497 mg, 2.32 mmol) in water was added and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated, diluted with DCM, and washed with Na2S2O3 solution. The organic layer was dried over MgSO4, filtered, and concentrated. The crude product was purified by flash chromatography (30% ether/hexanes) to afford the title compound. LC-MS (IE, m/z): 191.3 [M+1]+.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with DCM
  4. washwashed with Na2S2O3 solution
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (30% ether/hexanes)

Sources & evidence

ORD record
ord-f6b6accc3afd415bbfa2c921d75cdccc
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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