Ethyl Acetate → HCID 23500554, compound

HRID 1835756Notes

Reaction equation

HRID 1835756 reaction equation
[CH3:1][CH2:2][CH2:3][CH:4]([CH:6]1[N:11]2[C:12](=[O:15])[O:13][N:14]=[C:10]2[CH2:9][CH2:8][CH2:7]1)C.CC[O:18]C(C)=O>O1CCOCC1.O.C(O)CCC.O=[Os](=O)(=O)=O>[O:15]=[C:12]1[N:11]2[CH:6]([CH2:4][CH2:3][CH2:2][CH:1]=[O:18])[CH2:7][CH2:8][CH2:9][C:10]2=[N:14][O:13]1

Participants

7

Reactant 2

HCID 8857Ethyl AcetateHCID 23500572HCID 23500572, compound

Product 1

HCID 23500554HCID 23500554, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 2631-ButanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Ex-28) The product of Example 27 (0.42 g; 2 mmol) and NaIO4 (0.86 g; 4 mmol) were dissolved in a mixture of 12 mL of dioxane and 8 mL of H2O. Two drops of a 2% solution of OsO4 in n-butanol was added to the mixture. The reaction mixture was stirred until tlc (100% EtOAc) indicated that the starting material was consumed. A precipitate had formed and was filtered. This solid was washed with dioxane. The filtrate was concentrated and the residue was partitioned between H2O/CH2Cl2. The organic layer was dried over MgSO4 and concentrated to afford the title compound as an oil.

Workup

  1. customwas consumed
  2. customA precipitate had formed
  3. filtrationwas filtered
  4. washThis solid was washed with dioxane
  5. concentrationThe filtrate was concentrated
  6. customthe residue was partitioned between H2O/CH2Cl2
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d03f06fcc6cb4fcdafa7ec91aef86062
Source dataset
uspto-grants-2004_08
Patent number
US06774126B2

Reaction notes

Loading…