Acetic Acid → HCID 53726019, compound

HRID 322204Notes

Reaction equation

HRID 322204 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([CH:9]1[C:14](=[O:15])[O:13][C:12]([CH3:17])(C)O[C:10]1=O)=[O:8].OCC[C:22]#[N:23].C(=O)=O.[N+:27]([C:30]1[CH:37]=[CH:36][C:33](C=O)=[CH:32][CH:31]=1)([O-:29])=[O:28].N1CCCCC1.C(O)(=O)C>CC(O)C>[C:22]([CH2:17][CH2:12][O:13][C:14](=[O:15])[C:9](=[CH:10][C:33]1[CH:36]=[CH:37][C:30]([N+:27]([O-:29])=[O:28])=[CH:31][CH:32]=1)[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])#[N:23]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 280Carbon DioxideHCID 5414-NitrobenzaldehydeHCID 8011HydracrylonitrileHCID 8082PiperidineHCID 23004044HCID 23004044, compound

Product 1

HCID 53726019HCID 53726019, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5-(5-Methoxypentanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was heated with 3-hydroxypropionitrile (2.79 g, 39.2 mmol) at 80° C. until no more CO2 was released. After cooling to room temperature, the mixture was diluted with 50 ml of 2-propanol and 4-nitrobenzaldehyde (5.40 g, 35.6 mmol), piperidine (150 mg, 1.78 mmol) and acetic acid (110 mg, 1.78 mmol) was added, the mixture was stirred at room temperature for 48 hrs. After evaporation of solvent, the product was purified by chromatography (SiO2, MeOH:CHCl2=5:95). 7-Methoxy-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester was obtained as a pale-yellow oil (7.75 g, 60% yield).

Workup

  1. additionwas added
  2. customAfter evaporation of solvent
  3. customthe product was purified by chromatography (SiO2, MeOH:CHCl2=5:95)

Sources & evidence

ORD record
ord-d12d1ebaa67648c8a9fa1d82eef4516c
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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