1,4-Dioxane → HCID 12083068, compound

HRID 1168847Notes

Reaction equation

HRID 1168847 reaction equation
[CH2:1]([C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][N:6]=1)[CH2:2][CH:3]=C.[O:14]1CCOCC1.I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O.C(OCC)(=O)C>[O:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:5]([CH2:1][CH2:2][CH:3]=[O:14])=[N:6]1

Participants

7

Reactant 3

HCID 312751,4-DioxaneHCID 12083067HCID 12083067, compoundHCID 23667635Sodium periodate

Product 1

HCID 12083068HCID 12083068, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Compound 26 (549 mg, 3.2 mmol), water (5 mL), 1,4-dioxane (15 mL) and osmium tetroxide (15 mg, 0.06 mmol) were stirred for 5 min. in a small flask. Sodium metaperiodate (1.56 g, 7.3 mmol) was added over 30 min. and the suspension was then stirred for 1 hour. Ethyl acetate and water were added. The phases were separated and the aqueous phase was extracted with ethyl acetate and dichloromethane. The combined organic phases were dried over magnesium sulphate and evaporated to dryness to produce 784 mg of crude 27, which was used directly without further purification in the synthesis compound 28.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate and dichloromethane
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. customevaporated to dryness
  5. customto produce 784 mg of crude 27, which
  6. customwas used directly without further purification in the synthesis compound 28

Sources & evidence

ORD record
ord-16cbe03f2e3744d1a53ad3cfe2498431
Source dataset
uspto-grants-2003_09
Patent number
US06627645B2

Reaction notes

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