Diethyl Malonate → HCID 66767047, compound

HRID 1662016Notes

Reaction equation

HRID 1662016 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]/[N:9]=[CH:10]/[CH:11]=O)=[CH:4][CH:3]=1.[C:13](OCC)(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].N1CCCCC1.CCOC(C)=O>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:20])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 87141418HCID 87141418, compound

Product 1

HCID 66767047HCID 66767047, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crude (E)-2-(2-(4-fluorophenyl)hydrazono)acetaldehyde (0.97 g, 5.8 mmol) is dissolved in EtOH (50 mL), and diethyl malonate (0.93 g, 5.8 mmol) and piperidine (0.2 mL, 2.0 mmol) are added. The mixture is heated at reflux overnight. The reaction mixture is then cooled and concentrated. The residue is diluted with water and extracted with EtOAc twice. The combined organic extracts are dried over Na2SO4 and concentrated. The residue is purified by column chromatography on silica gel, eluting with PE:EtOAc (from 3:1 to 1:1), to afford title compound (0.26 g, 17% yield of two steps) MS (m/z): 263 (M+H).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture is then cooled
  4. concentrationconcentrated
  5. additionThe residue is diluted with water
  6. extractionextracted with EtOAc twice
  7. dry with materialThe combined organic extracts are dried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue is purified by column chromatography on silica gel
  10. washeluting with PE

Sources & evidence

ORD record
ord-4ef134091c4d4d6cb1d97354fa3bd409
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

Loading…