Water → HCID 13737690, compound

HRID 2229587Notes

Reaction equation

HRID 2229587 reaction equation
[CH:1]12[O:6][CH:2]1[CH2:3][CH2:4][CH2:5]2.O.[N-:8]=[N+:9]=[N-:10].[Na+].[Cl-].[NH4+]>C(O)C>[N:8]([C@@H:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[OH:6])=[N+:9]=[N-:10]

Participants

6

Reactant 4

HCID 962WaterHCID 92446-Oxabicyclo[3.1.0]hexaneHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 13737690HCID 13737690, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyclopentene oxide (5 g) was dissolved in ethanol (100 ml) and water (25 ml) and treated with sodium azide (3.9 g) and ammonium chloride (3.2 g) at reflux for 8 h. the mixture was cooled, excess solvent evaporated off at reduced pressure and extracted with ether. The organic solution was washed with water, dried (MgSO4) and evaporated. The residues were taken up in hexane, washed with water to remove any remaining ethanol, dried (MgSO4) and evaporated to give trans-1-azidocyclopentan-2-ol 3.6 g.

Workup

  1. temperatureat reflux for 8 h. the mixture
  2. temperaturewas cooled
  3. customexcess solvent evaporated off at reduced pressure
  4. extractionextracted with ether
  5. washThe organic solution was washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. washwashed with water
  9. customto remove any remaining ethanol
  10. dry with materialdried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-df06f01a72bb4747bef5457b2fd710e7
Source dataset
uspto-grants-2002_07
Patent number
US06420438B1

Reaction notes

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