Water → HCID 10899575, compound

HRID 1620786Notes

Reaction equation

HRID 1620786 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([O:11][Si](C(C)C)(C(C)C)C(C)C)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[N-:22]=[N+:23]=[N-:24].[Na+].[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[Ce].O>C(#N)C>[N:22]([CH:7]1[C:8](=[O:11])[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6]1)=[N+:23]=[N-:24]

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 407333Cerate(2-), hexakis(nitrato-kappaO)-, potassium (1:2), (OC-6-11)-HCID 11120552HCID 11120552, compound

Product 1

HCID 10899575HCID 10899575, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of (1,4-dioxaspiro[4.5]dec-7-en-8-yloxy) [tri(propan-2-yl)]silane (22.9 g) in acetonitrile (180 mL) were added dropwise sodium azide (21.4 g) and ammonium hexanitratocerate (IV) (121 g) at −20° C. The reaction mixture was stirred at −20° C. for 4 hr, ice-cooled water was added, and the mixture was extracted with diethyl ether. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (11.5 g).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-b99e2f6cdde348689ac455ffcb8be3a7
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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