Acetone → HCID 18429350, compound

HRID 1280143Notes

Reaction equation

HRID 1280143 reaction equation
[N+:1]([C:4]1[CH:5]=C([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)C=C)([O-:3])=[O:2].C[N+]1([O-])CC[O:19]CC1.[CH3:23][C:24]([CH3:26])=[O:25]>O.O=[Os](=O)(=O)=O>[OH:25][CH:24]([C:26]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=1)[CH2:23][OH:19]

Participants

6

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 121925533,5-Dinitrostyrene

Product 1

HCID 18429350HCID 18429350, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

3,5-Dinitrostyrene (0.50 g, 2.58 mmol) was dissolved in a mixture of acetone and water (8:1, 70 ml) and the solution was cooled to 0° C. OsO4 (0.046 g, 0.18 mmol) and NMO (0.60 g, 5.15 mmol) were added and the solution was stirred at room temperature for 16 h. A solution of Na2S2O5 (1.5 g) in water (120 ml) was added and the organic solvent removed by evaporation. The aqueous phase was extracted with ethyl acetate (2×70 ml) and the combined organic phases were dried (Na2SO4) and evaporated. The product was purified by preparative HPLC. Yield: 0.44 g (75%).

Workup

  1. customthe organic solvent removed by evaporation
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×70 ml)
  3. dry with materialthe combined organic phases were dried (Na2SO4)
  4. customevaporated
  5. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-0e050a997db84b2ea29226c48cc3a748
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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