Nitromethane → HCID 11275397, compound

HRID 458007Notes

Reaction equation

HRID 458007 reaction equation
[NH:1]1[C:5]([CH2:6][C:7]2(C#N)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=NN=N1.[N+:15]([CH3:18])([O-:17])=[O:16].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[N+:15]([CH2:18][C:7]1([CH2:6][C:5]#[N:1])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([O-:17])=[O:16]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 2724141Tetrabutylammonium FluorideHCID 178509433HCID 178509433, compound2×

Product 1

HCID 11275397HCID 11275397, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The nitrile (compound 2, 0.78 g, 6.44 mmol), nitromethane (0.80 g, 13.11 mmol) and tetrabutyl ammonium fluoride (1.0 M in tetrahydrofuran, 10 mL, 10 mmol) were heated in 20 mL tetrahydrofuran to 70° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with dilute hydrochloric acid and water, dried over magnesium sulphate, filtered, and evaporated to dryness. The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 3:1 to give the required product as a yellow oil (0.83 g, 71%).

Workup

  1. washwashed with dilute hydrochloric acid and water
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography on silica eluting with heptane/ethyl acetate 3:1

Sources & evidence

ORD record
ord-93d5e0f6971d4be6ad999c693711a8f2
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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