1,4-Dioxane → HCID 12083068, compound

HRID 1293103Notes

Reaction equation

HRID 1293103 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-14ca5a5c19a64bff9c40d31101175166
Source dataset
uspto-grants-2007_07
Patent number
US07238713B2

Reaction notes

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