Nitromethane → HCID 11275397, compound

HRID 1058926Notes

Reaction equation

HRID 1058926 reaction equation
[C:1]1(=[CH:7][C:8]#[N:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:10]([CH3:13])([O-:12])=[O:11].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[N+:10]([CH2:13][C:1]1([CH2:7][C:8]#[N:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 97105Acetonitrile, cyclohexylidene-2×HCID 2724141Tetrabutylammonium Fluoride

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-a0665b23c244492baba70572d1073813
Source dataset
uspto-grants-2003_02
Patent number
US06518289B1

Reaction notes

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