1,4-Dioxane → HCID 57585674, compound

HRID 2233342Notes

Reaction equation

HRID 2233342 reaction equation
[CH2:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11](=[O:14])[CH:10]=[CH:9]2)[CH:2]=C.[O:15]1CCOCC1>O.O=[Os](=O)(=O)=O>[O:14]=[C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[C:4]([CH2:1][CH:2]=[O:15])[CH:5]=[CH:6][CH:7]=2)[O:12]1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 4547045HCID 4547045, compound

Product 1

HCID 57585674HCID 57585674, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

To a solution of 8-(2-propen-1-yl)-2H-chromen-2-one (390 mg, 2.0 mmol) in dioxane (10 mL) and water (5 mL) was added OsO4 (4% solution in H2O, 0.5 mL, 10 mol %) and NaIO4 (430 mg, 4.0 mmol). The reaction was stirred at RT for 2 h and NaIO4 (430 mg, 4.0 mmol) was added and the reaction was allowed to stir another 2 h. The reaction was diluted with 20 mL of H2O and was extracted with ethyl acetate (3×50 mL). The combined extracts were dried (Na2SO4), and concentrated to give the title compound (350 mg, 93%) as a dark oil which was used without further purification: MS (ES) m/e 188.9 (M+H)+.

Workup

  1. stirringto stir another 2 h
  2. extractionwas extracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e26e4cd89f674e5886c0b50459e9fd5b
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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