Pinacolone → 4,4-Dimethyl-1-(3-pyridinyl)-1-penten-3-one

HRID 443841Notes

Reaction equation

HRID 443841 reaction equation
[OH-].[Na+].[CH3:3][C:4]([CH3:9])([CH3:8])[C:5](=[O:7])[CH3:6].[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=O)[CH:11]=1>O>[CH3:3][C:4]([CH3:9])([CH3:8])[C:5](=[O:7])[CH:6]=[CH:16][C:12]1[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6416PinacoloneHCID 103713-PyridinecarboxaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 536634384,4-Dimethyl-1-(3-pyridinyl)-1-penten-3-oneYield 51.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 ml of 10% strength sodium hydroxide solution were added to a solution of 35 g (0.35 mol) of 3,3-dimethylbutan-2-one and 38 g (0.355 mol) of 3-pyridinealdehyde in 2,000 ml of water and the solution was stirred overnight at room temperature. The crystalline precipitate was filtered off, dried and recrystallized from n-hexane. 34.1 g (51.5% of theory) of 4,4-dimethyl-1-pyridin-3-yl-1-penten-3-one of melting point 68°-70° C. were obtained. ##STR117##

Workup

  1. filtrationThe crystalline precipitate was filtered off
  2. customdried
  3. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-aa688f295efc489682c81ab5bf262c8a
Source dataset
uspto-grants-1981_04
Patent number
US04262000

Reaction notes

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