Nitromethane → 3-(NITROMETHYL)CYCLOPENTANONE

HRID 1761744Notes

Reaction equation

HRID 1761744 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[N+:7]([CH3:10])([O-:9])=[O:8].N12CCCC1=NCCC2>C(O)(C)C>[N+:7]([CH2:10][CH:3]1[CH2:4][CH2:5][C:1](=[O:6])[CH2:2]1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 135882-Cyclopenten-1-oneHCID 763491,5-Diazabicyclo(4.3.0)non-5-ene

Product 1

HCID 119580463-(NITROMETHYL)CYCLOPENTANONEYield 88%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

100 g of 2-cyclopentenone are dissolved together with 666 ml of nitromethane and 5 g of 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) in 1.1 l of isopropanol, and the solution is left to stand at room temperature for 5 h. The isopropanol is then substantially distilled in vacuo, and the residue is dissolved in ethyl acetate and the solution is washed twice with 0.5 l of dilute sulphuric acid each time. The organic phase is dried with sodium sulphate and evaporated. In this way 154 g (88% of theory) of 3-(nitromethyl)cyclopentanone are obtained sufficiently pure for the next reaction.

Workup

  1. waitthe solution is left
  2. distillationThe isopropanol is then substantially distilled in vacuo
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washthe solution is washed twice with 0.5 l of dilute sulphuric acid each time
  5. dry with materialThe organic phase is dried with sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-66b41581cb2c4b5e894c96d13e3e8bb2
Source dataset
uspto-grants-1989_05
Patent number
US04827032

Reaction notes

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