6-Oxabicyclo[3.1.0]hexane → 2-(2-Nitro-1H-imidazol-1-yl)cyclopentan-1-ol

HRID 1463041Notes

Reaction equation

HRID 1463041 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[CH:9]12[O:14][CH:10]1[CH2:11][CH2:12][CH2:13]2.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:14][CH:10]1[CH2:11][CH2:12][CH2:13][CH:9]1[N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 107012-NitroimidazoleHCID 11430Potassium Carbonate

Product 1

HCID 155918462-(2-Nitro-1H-imidazol-1-yl)cyclopentan-1-olYield 47.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 0.339 g (3 mmol) of 2-nitroimidazole, 30 ml of ethanol, 3.5 ml of cyclopentene oxide and 0.15 g of potassium carbonate was refluxed with stirring under nitrogen for 20 hr. A clear yellow solution resulted; this was evaporated and the residue dissolved in 50 ml of chloroform and filtered. The filtrate was evaporated to yield 0.28 g (47.3%) of the title compound. It was recrystallized from ethyl acetate, mp 109° C.

Workup

  1. temperaturewas refluxed
  2. customA clear yellow solution resulted
  3. customthis was evaporated
  4. dissolutionthe residue dissolved in 50 ml of chloroform
  5. filtrationfiltered
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-d317cafbc6da40f283077557698d9be1
Source dataset
uspto-grants-1984_07
Patent number
US04462992

Reaction notes

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