Methyl cyanoacetate → methyl (E)-3-(2,4-dibenzyloxyphenyl)-2-cyanoacrylate

HRID 322934

Reaction equation

HRID 322934 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([CH2:27][C:28]([O:30][CH3:31])=[O:29])#[N:26].N1CCCCC1>C(O)C>[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:14]=[CH:13][C:10]=1/[CH:11]=[C:27](\[C:25]#[N:26])/[C:28]([O:30][CH3:31])=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 8082PiperidineHCID 18090802,4-Bis(benzyloxy)benzaldehyde

Product 1

HCID 86756581methyl (E)-3-(2,4-dibenzyloxyphenyl)-2-cyanoacrylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4-dibenzyloxybenzaldehyde (1 g), methyl cyanoacetate (0.27 mL), piperidine (0.1 mL) and ethanol (30 mL) is stirred at ambient temperature for 20 minutes and the solvent is removed under reduced pressure. The residue is recrystallized from ethanol to give methyl (E)-3-(2,4-dibenzyloxyphenyl)-2-cyanoacrylate as a yellow solid (400 mg).

Workup

  1. customthe solvent is removed under reduced pressure
  2. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-c5088d268910443a81fef21ea2bc3c30
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Linked notes

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