Cyclopropyl methyl ketone → 1-Cyclopropyl-3-(pyridin-4-yl)-1,3-propanedione

HRID 1973348Notes

Reaction equation

HRID 1973348 reaction equation
[C:1]([O:9]C)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH:11]1([C:14]([CH3:16])=[O:15])[CH2:13][CH2:12]1.C[O-].[Na+]>C1C=CC=CC=1>[CH:11]1([C:14](=[O:15])[CH2:16][C:1]([C:2]2[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=2)=[O:9])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 13004Cyclopropyl methyl ketoneHCID 227085Methyl isonicotinateHCID 10942334Sodium Methoxide

Product 1

HCID 123605581-Cyclopropyl-3-(pyridin-4-yl)-1,3-propanedione

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 13.7 g. of methyl isonicotinate, 16.8 g. of cyclopropylmethyl ketone and 6 g. of sodium methoxide in 150 ml. of benzene is heated under reflux for 8 hours. The mixture is filtered and the collected solid is dissolved in water. The aqueous mixture is made weakly acidic with dilute hydrochloric acid and extracted with ether. The ethereal solution is dried over magnesium sulfate and concentrated under reduced pressure to give 1-cyclopropyl-3-(4-pyridyl)-1,3-propanedione as a mobile, yellow liquid, infra-red spectrum 6.15u (CHCl3, β-diketone.

Workup

  1. additionA mixture of 13.7 g
  2. temperatureunder reflux for 8 hours
  3. filtrationThe mixture is filtered
  4. dissolutionthe collected solid is dissolved in water
  5. extractionextracted with ether
  6. dry with materialThe ethereal solution is dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1a1961022a74e98a7bbd175a262ee10
Source dataset
uspto-grants-1976_12
Patent number
US03997530

Reaction notes

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