Piperidine → Methyl 2-(2-cyanobenzylidene)-4,4-dimethoxyacetoacetate

HRID 1164651Notes

Reaction equation

HRID 1164651 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O)#[N:2].[CH3:11][O:12][CH:13]([O:21][CH3:22])[C:14](=[O:20])[CH2:15][C:16]([O:18][CH3:19])=[O:17].N1CCCCC1>C1C=CC=CC=1.C(O)(=O)C>[C:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[C:15]([C:14]([CH:13]([O:12][CH3:11])[O:21][CH3:22])=[O:20])[C:16]([O:18][CH3:19])=[O:17])#[N:2]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 1012092-CyanobenzaldehydeHCID 11008445Methyl 4,4-dimethoxy-3-oxobutanoate

Product 1

HCID 53675930Methyl 2-(2-cyanobenzylidene)-4,4-dimethoxyacetoacetateYield 36.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent2×

Procedure

A benzene solution (120 ml) of 2-cyanobenzaldehyde (30.97 g), methyl 4,4-dimethoxyacetoacetate (46.14 g), acetic acid (2.3 g) and piperidine (2.4 g) was refluxed under heating for 8 hours. After addition of benzene (80 ml) and washing with water, the solution was treated with an activated charcoal. The evaporated residue was chromatographed on silica gel (500 g) with methylene chloride as an eluent. The fractions containing a desired compound were collected and evaporated to give methyl 2-(2-cyanobenzylidene)-4,4-dimethoxyacetoacetate (25.16 g).

Workup

  1. temperatureunder heating for 8 hours
  2. washwashing with water
  3. additionthe solution was treated with an activated charcoal
  4. customThe evaporated residue was chromatographed on silica gel (500 g) with methylene chloride as an eluent
  5. additionThe fractions containing a desired compound
  6. customwere collected
  7. customevaporated

Sources & evidence

ORD record
ord-99218264995843b0a09f087139738dcf
Source dataset
uspto-grants-1983_01
Patent number
US04370334

Reaction notes

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