Ethyl cyanoacetate → 2-Propenoic acid, 2-cyano-3-(4-cyanophenyl)-, ethyl ester

HRID 1766349Notes

Reaction equation

HRID 1766349 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]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12].N1CCCCC1>C(O)C>[CH2:17]([O:16][C:14](=[O:15])[C:13]([C:11]#[N:12])=[CH:7][C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH3:18]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 660424-Cyanobenzaldehyde

Product 1

HCID 3670612-Propenoic acid, 2-cyano-3-(4-cyanophenyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Cyanobenzaldehyde (3.00 g, 22.9 mmol) ad ethyl cyanoacetate (2.59 g, 22.9 mmol) are dissolved in absolute ethanol (100 ml). Piperidine (0.097 g, 1.14 mmol) is added, and the solution is stirred at room temperature until no more starting material is apparent by tic. This takes approx. 2 hours during which time a precipitate is formed. The precipitate is filtered and recrystallised, or alternatively, the crude reaction mixture is concentrated in vacuo and chromatographed over silica with cyclohexane/ethyl acetate mixtures as eluent to yield a white solid.

Workup

  1. customThis takes approx. 2 hours during which time a precipitate is formed
  2. filtrationThe precipitate is filtered
  3. customrecrystallised
  4. customalternatively, the crude reaction mixture
  5. concentrationis concentrated in vacuo
  6. customchromatographed over silica with cyclohexane/ethyl acetate
  7. customto yield a white solid

Sources & evidence

ORD record
ord-6481639f81844518b0a047ed27ccd219
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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