Oxolane--water (1/1) → HCID 86714089, compound

HRID 576412Notes

Reaction equation

HRID 576412 reaction equation
[CH3:1][N:2]([CH3:26])[C:3](=[O:25])[S:4][C:5]1[C:10]([Cl:11])=[C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:8]=[C:7]([Br:21])[C:6]=1[CH2:22][CH:23]=C.C1C[O:30]CC1.O>O=[Os](=O)(=O)=O>[CH3:26][N:2]([CH3:1])[C:3](=[O:25])[S:4][C:5]1[C:10]([Cl:11])=[C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:8]=[C:7]([Br:21])[C:6]=1[CH2:22][CH:23]=[O:30]

Participants

4

Reactant 2

HCID 21881883Oxolane--water (1/1)HCID 89284006HCID 89284006, compound

Product 1

HCID 86714089HCID 86714089, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 218 (1.48 g, 3.25 mmol) in THF/water (15 mL/15 mL) were added NaIO4 (2.78 g, 13.02 mmol) and OsO4 (0.4 mL, 2.5% in isopropanol). After stirring at rt overnight, the reaction was quenched with saturated Na2SO3 solution (20 mL), and the mixture was extracted with ethyl acetate (50 mL×2). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude product 219 was dried under high vacuum and used without further purification (1.57 g, 3.44 mmol, 106%).

Workup

  1. customthe reaction was quenched with saturated Na2SO3 solution (20 mL)
  2. extractionthe mixture was extracted with ethyl acetate (50 mL×2)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dry with materialThe crude product 219 was dried under high vacuum
  8. customused without further purification (1.57 g, 3.44 mmol, 106%)

Sources & evidence

ORD record
ord-a7beb1af8dba48cfb49e518c75bace9e
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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