Water → HCID 15417111, compound

HRID 988005Notes

Reaction equation

HRID 988005 reaction equation
[S:1](Cl)(Cl)=[O:2].[CH2:5]([O:12][CH2:13][C@@H:14]([OH:28])[CH2:15][CH2:16][C@H:17]([OH:27])[CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.I([O-])(=O)(=O)=[O:30].[Na+].O>ClC(Cl)(Cl)Cl>[CH2:20]([O:19][CH2:18][C@@H:17]1[CH2:16][CH2:15][C@@H:14]([CH2:13][O:12][CH2:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:28][S:1](=[O:2])(=[O:30])[O:27]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 15739467HCID 15739467, compoundHCID 23667635Sodium periodate

Product 1

HCID 15417111HCID 15417111, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1.43 g (12 mmol) of thionyl chloride were slowly added to 3.30 g (10 mmol) of the diol 5 in 70 ml of dry tetrachloromethane under an argon atmosphere, and the mixture was then refluxed for 90 minutes. After removal of the solvent in a rotary evaporator, the residue was taken up in a mixture of tetrachloromethane (40 ml), acetonitrile (40 ml) and water (60 ml) and, at 0° C., 15 mg (72 μmol) of RuCl3*3H2O and 4.28 g (20 mmol) of sodium periodate were added. The mixture was then left to stir at room temperature for one hour, and then 50 ml of water were added to the suspension. Subsequent extraction with diethyl ether (3×75 ml) and washing of the organic phase with saturated NaCl solution (100 ml), followed by drying (Na2SO4), resulted in a residue which on column chromatography (n-hexane:AcOEt=2:1, Rf=0.20) afforded compound 7 in a yield of 3.37 g (86%).

Workup

  1. temperaturethe mixture was then refluxed for 90 minutes
  2. customAfter removal of the solvent
  3. customin a rotary evaporator
  4. additionthe residue was taken up in a mixture of tetrachloromethane (40 ml), acetonitrile (40 ml) and water (60 ml) and, at 0° C.
  5. waitThe mixture was then left
  6. extractionSubsequent extraction with diethyl ether (3×75 ml)
  7. washwashing of the organic phase with saturated NaCl solution (100 ml)
  8. dry with materialby drying (Na2SO4)
  9. customresulted in a residue which on column chromatography (n-hexane:AcOEt=2:1, Rf=0.20)

Sources & evidence

ORD record
ord-91ac910753e341a5a71205b6b2c50f8e
Source dataset
uspto-grants-2003_10
Patent number
US06632953B1

Reaction notes

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