Cyclohexene oxide → HCID 10953608, compound

HRID 1509853Notes

Reaction equation

HRID 1509853 reaction equation
[CH:1]12[O:7][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2]2.[N-:8]=[N+:9]=[N-:10].[Na+]>CC(C)=O.O>[N:8]([CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][CH:1]1[OH:7])=[N+:9]=[N-:10]

Participants

5

Reactant 2

HCID 9246Cyclohexene oxideHCID 33557Sodium Azide

Product 1

HCID 10953608HCID 10953608, compoundYield 10.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 7-oxa-bicyclo[4.1.0]heptane (0.300 g, 3.06 mmol) in acetone (3 mL) was added sodium azide (0.504 g, 7.75 mmol) in water (3 mL). The reaction mixture was refluxed for 12 h. The acetone was removed in vacuo and the product was extracted with ethyl acetate (5 mL). The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and concentrated to provide the title compound (46 mg).

Workup

  1. temperatureThe reaction mixture was refluxed for 12 h
  2. customThe acetone was removed in vacuo
  3. extractionthe product was extracted with ethyl acetate (5 mL)
  4. customThe organic layer was collected
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-92cdde38cc274b9db820beafc2171cec
Source dataset
uspto-grants-2012_07
Patent number
US08211894B2

Reaction notes

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