Ethyl cyanoacetate → HCID 53920535, compound

HRID 742328Notes

Reaction equation

HRID 742328 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.[C:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])#[N:17].C([O-])(=O)C.[NH4+]>C(O)(=O)C.O.C1C=CC=CC=1>[CH2:22]([O:21][C:19]([C:18](=[C:6]([C:5]1[CH:14]=[CH:15][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:16]#[N:17])=[O:20])[CH3:23]

Participants

7

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 86524-MethylbenzophenoneHCID 517165Ammonium Acetate2×

Product 1

HCID 53920535HCID 53920535, compoundYield 74.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 10 g (51 mmol) of 4-methylbenzophenone, 4.9 mL (46 mL (46 mmol) of ethyl cyanoacetate, 0.72 g (9.3 mmol) of ammonium acetate, 2.2 mL (37 mmol) of acetic acid and 8 mL of benzene was heated at reflux for 18 h using a Dean-Stark water separator. Then, 1.1 mL of acetic acid and 0.35 g of ammonium acetate was added and the mixture was heated for 24 h more. The solvent was removed and the residue was dissolved in chloroform and washed with water. The organic phase was dried over magnesium sulfate and the solvent was removed to yield a crude product. This was chromatographed on silica gel (hexane-ethyl acetate mixtures of increasing polarity) to afford 10 g of the title compound of the example as a colourless oil (yield: 67%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperaturethe mixture was heated for 24 h more
  4. customThe solvent was removed
  5. dissolutionthe residue was dissolved in chloroform
  6. washwashed with water
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. customthe solvent was removed
  9. customto yield a crude product
  10. customThis was chromatographed on silica gel (hexane-ethyl acetate mixtures of increasing polarity)

Sources & evidence

ORD record
ord-17bc3c9e7e554c72bbb4f962b5232c4a
Source dataset
uspto-grants-1996_09
Patent number
US05554624

Reaction notes

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