Ethyl Acetate → HCID 86602835, compound

HRID 644946Notes

Reaction equation

HRID 644946 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][C:11](=C)[CH2:10][C@H:9]2[C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:22]CC1.I([O-])(=O)(=O)=O.[Na+].C(OCC)(=O)C>CC(C)=O.O.O1CCCC1.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][C:11](=[O:22])[CH2:10][C@H:9]2[C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 86602834HCID 86602834, compound

Product 1

HCID 86602835HCID 86602835, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A 50 mL round bottom flask equipped with a magnetic stir bar was charged with 1.20 g (4.8 mmol) of the product of Step B dissolved in 8.6 mL acetone. To the reaction mixture was added 0.673 g (5.74 mmol) of 4-methylmorpholine N-oxide dissolved in 2 mL water followed by 1.52 mL (0.20 mmol) of an osmium tetroxide solution (4 wt % in water). The reaction mixture was stirred 1 h at room temperature at which point TLC analysis indicated complete consumption of the starting material. The reaction mixture was quenched with excess 10% aqueous sodium bisulfite, then partitioned between water and ethyl acetate in a separatory funnel. The organic layer was washed with water, separated, dried (MgSO4), filtered and evaporated in vacuo. The residual oil was redissolved in 5.5 mL tetrahydrofuran in a 25 mL round bottom flask and 5.5 mL water was added. To this solution was added 1.228 g (5.74 mmol) of sodium periodate. After stirring for approximately 10 min at room temperature, a precipitate formed and the suspension was diluted with 5 mL tetrahydrofuran. Stirring was continued for 1 h, at which point TLC analysis revealed a new less polar product spot. The mixture was suspended between ethyl acetate and water and extracted. The organic layer was separated, dried (MgSO4), filtered and evaporated in vacuo. The residual clear oil was used in the next step without further purification.

Workup

  1. customA 50 mL round bottom flask equipped with a magnetic stir bar
  2. customconsumption of the starting material
  3. customThe reaction mixture was quenched with excess 10% aqueous sodium bisulfite
  4. custompartitioned between water and ethyl acetate in a separatory funnel
  5. washThe organic layer was washed with water
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. dissolutionThe residual oil was redissolved in 5.5 mL tetrahydrofuran in a 25 mL round bottom flask
  11. addition5.5 mL water was added
  12. stirringAfter stirring for approximately 10 min at room temperature
  13. customa precipitate formed
  14. stirringStirring
  15. waitwas continued for 1 h, at which point TLC analysis
  16. extractionextracted
  17. customThe organic layer was separated
  18. dry with materialdried (MgSO4)
  19. filtrationfiltered
  20. customevaporated in vacuo
  21. customThe residual clear oil was used in the next step without further purification

Sources & evidence

ORD record
ord-b72685301d874ba58c89e4c6cf7ad52d
Source dataset
uspto-grants-2010_04
Patent number
US07700778B2

Reaction notes

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