2-(4-Chlorophenoxy)-4,4-dimethyl-1-pyridin-3-yl-1-penten-3-one → 2-(4-Chlorophenoxy)-4,4-dimethyl-1-pyridin-3-yl-pentan-3-one

HRID 443845Notes

Reaction equation

HRID 443845 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]([C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH:7]([C:15](=[O:20])[C:16]([CH3:18])([CH3:19])[CH3:17])[CH2:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 542410592-(4-Chlorophenoxy)-4,4-dimethyl-1-pyridin-3-yl-1-penten-3-one

Product 1

HCID 234659262-(4-Chlorophenoxy)-4,4-dimethyl-1-pyridin-3-yl-pentan-3-oneYield 62%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

32 g (0.49 mol) of zinc dust were added to 48 g (0.152 mol) of 2-(4-chlorophenoxy)-4,4-dimethyl-1-pyridin-3-yl-1-penten-3-one, dissolved in 170 ml of glacial acetic acid, and the mixture was heated under reflux on an oil bath for 40 minutes. The zinc was filtered off from the solution and rinsed with glacial acetic acid and the acetic acid solution was concentrated. The residue was rendered alkaline with 1 N sodium hydroxide solution and extracted three times with ethyl acetate. From the ethyl acetate phase, 29.9 g (62% of theory) of 2-(4-chlorophenoxy)-4,4-dimethyl-1-pyridin-3-yl-pentan-3-one of melting point 77°-79° C. were obtained after recrystallization from cyclohexane.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux on an oil bath for 40 minutes
  3. filtrationThe zinc was filtered off from the solution
  4. washrinsed with glacial acetic acid
  5. concentrationthe acetic acid solution was concentrated
  6. extractionextracted three times with ethyl acetate

Sources & evidence

ORD record
ord-29cc2473f3794cc482ffc2a857c5fa36
Source dataset
uspto-grants-1981_04
Patent number
US04262000

Reaction notes

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