Acetone → HCID 89767744, compound

HRID 591511Notes

Reaction equation

HRID 591511 reaction equation
[C:1]([O:7][C:8]1[CH:21]=[C:20]([CH:22]=C)[C:11]2[C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:13][S:14][C:10]=2[CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].CC(C)=[O:26].C[N+]1([O-])CCOCC1>O=[Os](=O)(=O)=O.O.CC#N>[C:1]([O:7][C:8]1[CH:21]=[C:20]([CH:22]=[O:26])[C:11]2[C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:13][S:14][C:10]=2[CH:9]=1)(=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5]

Participants

7

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 89767870HCID 89767870, compound

Product 1

HCID 89767744HCID 89767744, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-(2-methoxy-2-oxoethyl)-4-vinyl-1-benzothiophen-6-yl pivalate (480 mg), acetone (500 μL), water (500 μL) and CH3CN (500 μL) were added OsO4 (7% microcapsule, 524 mg) and NMO (507 mg) at room temperature. The mixture was stirred at room temperature for 20 h. The insoluble material was removed by filtration, and the filtrate was concentrated in vacuo. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. To a mixture of the residue, THF (3 mL) and water (3 mL) was added NaIO4 (403 mg, 1.88 mmol) at room temperature. After stirring at room temperature for 1 h, the m mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (152 mg).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe mixture was poured into water at room temperature
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed successively with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. additionTo a mixture of the residue, THF (3 mL) and water (3 mL)
  10. stirringAfter stirring at room temperature for 1 h
  11. extractionextracted with EtOAc
  12. customThe organic layer was separated
  13. washwashed successively with water and brine
  14. dry with materialdried over MgSO4
  15. concentrationconcentrated in vacuo
  16. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-cdf5e34868ad455ab9704987f1eba959
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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