Pyridine → HCID 10176785, compound

HRID 1721126Notes

Reaction equation

HRID 1721126 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13]C([O-])=O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]1([C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)/[C:4](=[CH:13]/[C:12]([O:18][CH2:19][CH3:20])=[O:17])/[O:6]1)=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6811Phthalic AnhydrideHCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 10176785HCID 10176785, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

59.2 g (0.4 mol) of phthalic anhydride, 26.4 g (0.2 mol) of monoethyl malonate, and 15.8 g (0.2 mol) of pyridine are added to 200 ml of toluene, and the reaction mixture is heated under reflux for 4 hours. After terminating the reaction, 100 ml of water is added to the reaction mixture, and an organic layer is separated out. The organic layer is washed with 100 ml of 5%-aqueous acetic acid solution, and toluene is distilled off under a reduced pressure. The residue thus obtained is recrystallized from ethanol, to give 32.7 g (0.15 mol) of ethyl (Z)-3-phthalidylideneacetate. The yield is 75.0%.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 4 hours
  3. customAfter terminating
  4. customthe reaction, 100 ml of water
  5. additionis added to the reaction mixture
  6. customan organic layer is separated out
  7. washThe organic layer is washed with 100 ml of 5%-aqueous acetic acid solution, and toluene
  8. distillationis distilled off under a reduced pressure
  9. customThe residue thus obtained
  10. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-91667e7b383c440c8cd7e28d8179a714
Source dataset
uspto-grants-1996_04
Patent number
US05508446

Reaction notes

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