Water → HCID 11137193, compound

HRID 459680Notes

Reaction equation

HRID 459680 reaction equation
C(Cl)(Cl)(Cl)Cl.[CH2:6]([C@H:9]1[O:11][C@H:10]1[CH2:12][OH:13])[CH2:7][CH3:8].C(Cl)Cl.[OH2:17]>>[CH2:6]([C@@H:9]1[O:11][C@@H:10]1[C:12]([OH:17])=[O:13])[CH2:7][CH3:8]

Participants

5

Reactant 4

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 6344DichloromethaneHCID 11007869HCID 11007869, compound

Product 1

HCID 11137193HCID 11137193, compoundYield 67%

Procedure

A flask was charged with 34 ml of CCl4, 34 ml of acetonitrle and 2 g of (2S, cis)-3-propyloxiranemethanol. Then 11 g of NaIO4 in 51 ml of water were added, followed by 86 mg of RuCl3 to this biphasic solution. The mixture was stirred vigorously for 3 hrs at RT and 100 ml of methylene chloride was added. The organic phase was separated and water phase was extracted with methylene chloride. The combined black organic phase was dried over MgSO4 and concentrated. The residue was diluted with ether and filtered through celite to give colorless solution. After evaporation of solvent a pure product was obtained (yield 67%).

Workup

  1. customThe organic phase was separated
  2. extractionwater phase was extracted with methylene chloride
  3. dry with materialThe combined black organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. additionThe residue was diluted with ether
  6. filtrationfiltered through celite
  7. customto give colorless solution
  8. customAfter evaporation of solvent a pure product
  9. customwas obtained (yield 67%)

Sources & evidence

ORD record
ord-97b6c392e5594f8bb3d2e25538f2e084
Source dataset
uspto-grants-2007_03
Patent number
US07195719B1

Reaction notes

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