p-Toluenesulfonic acid → HCID 5388617, compound

HRID 1766356Notes

Reaction equation

HRID 1766356 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[C:11]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:12][C:13]([CH3:15])=[O:14].N1CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:13](/[C:12](=[CH:7]/[C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)/[C:11]([O:17][CH2:18][CH3:19])=[O:16])(=[O:14])[CH3:15]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8082PiperidineHCID 8868Ethyl AcetoacetateHCID 660424-Cyanobenzaldehyde

Product 1

HCID 5388617HCID 5388617, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-cyanobenzaldehyde (2 g, 15.3 mmol), ethyl acetoacetate (1.98 g, 15.3 mmol), piperidine (65 mg, 0.76 mmol), and p-toluenesulfonic acid (131 mg, 0.76 mmol) in toluene (100 ml) is stirred under an argon atmosphere at reflux for 72 hours in a flask equipped with a Dean-Stark trap. The crude reaction mixture is concentrated in vacuo to afford an oil which is chromatographed over silica gel with cyclohexane/ethyl acetate 20:1 as eluent.

Workup

  1. temperatureat reflux for 72 hours in a flask
  2. customequipped with a Dean-Stark trap
  3. customThe crude reaction mixture
  4. concentrationis concentrated in vacuo
  5. customto afford an oil which
  6. customis chromatographed over silica gel with cyclohexane/ethyl acetate 20:1 as eluent

Sources & evidence

ORD record
ord-5d82bf28cd34442db283097e0f6aa368
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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