Acetonitrile → Benzoylacetonitrile

HRID 1749418Notes

Reaction equation

HRID 1749418 reaction equation
CO[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][C:12]#[N:13].[H-].[Na+]>C1COCC1>[O:10]=[C:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:11][C:12]#[N:13]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 7150Methyl BenzoateHCID 24758Sodium hydride

Product 1

HCID 64799Benzoylacetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of benzoic acid methyl ester (1.0 equiv.) and methyl cyanide (2.0 equiv.) in anhydrous THF (1.0 M) was added sodium hydride (60% in mineral oil, 2 equiv.) under nitrogen. After the resulting reaction mixture was stirred at 70° C. overnight, the reaction mixture was quenched with ice-water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. Concentration under vacuum afforded the crude product as a brown solid. 1H-NMR (400 MHz, CDCl3) δ (ppm) 7.94-7.92 (m, 2H), 7.69-7.65 (m, 1H), 7.55-7.54 (m, 2H), 4.08 (s, 2H).

Workup

  1. customAfter the resulting reaction mixture
  2. customthe reaction mixture was quenched with ice-water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-d2165186a844462daa2789132d2cc53b
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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