Nitromethane → 3-(NITROMETHYL)CYCLOPENTANONE

HRID 1200261Notes

Reaction equation

HRID 1200261 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-601b7ee1889742cbad7ae8f223928ca2
Source dataset
uspto-grants-1990_02
Patent number
US04904797

Reaction notes

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