Hydrochloric Acid → 3,9-Dioxaspiro[5.5]undecan-2-one

HRID 2223933Notes

Reaction equation

HRID 2223933 reaction equation
[CH:1]12B[CH:5]([CH2:6][CH2:7][CH2:8]1)CCC2.[O:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.[OH-:15].[Na+].[OH:17]O.Cl>O1CCCC1.C(O)C>[CH2:12]1[C:7]2([CH2:6][CH2:5][O:15][CH2:1][CH2:8]2)[CH2:13][CH2:14][O:10][C:11]1=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 178419114HCID 178419114, compound

Product 1

HCID 104873553,9-Dioxaspiro[5.5]undecan-2-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of methyl (4-vinyltetrahydropyran-4-yl) acetate (455 mg) in tetrahydofuran (3 mL) was added 0.5M 9-borabicyclo[3.3.1]-nonane/tetrahydrofuran (10.0 mL) dropwise over 10 minutes. The reaction solution was allowed for its temperature to rise to room temperature and it was stirred for additional 17 hours. The reaction solution was again ice-cooled and ethanol (2 mL), a 6N aqueous sodium hydroxide solution (4 mL) and 30% hydrogen peroxide (4 mL) were added thereto successively. The reaction solution was then allowed for its temperature to rise to room temperature and it was stirred for additional 30 minutes. The reaction solution was again ice-cooled. After addition of conc. hydrochloric acid (2.5 mL), the reaction solution was allowed for its temperature to rise to room temperature. The solution was stirred for additional 1 hour. The reaction solution was extracted with chloroform. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (7:3 to 6:4)] to give the title compound (271 mg).

Workup

  1. customto rise to room temperature
  2. temperaturecooled
  3. customto rise to room temperature
  4. stirringit was stirred for additional 30 minutes
  5. temperaturecooled
  6. customto rise to room temperature
  7. stirringThe solution was stirred for additional 1 hour
  8. extractionThe reaction solution was extracted with chloroform
  9. washThe organic layer was washed with saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (7:3 to 6:4)]

Sources & evidence

ORD record
ord-933442d242c246e08f289a4b06866db3
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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