Cyclopropyl methyl ketone → 1-Cyclopropyl-3-(pyridin-3-yl)propane-1,3-dione

HRID 1076684Notes

Reaction equation

HRID 1076684 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH:12]1([C:15]([CH3:17])=[O:16])[CH2:14][CH2:13]1.C[O-].[Na+]>C1C=CC=CC=1>[CH:12]1([C:15](=[O:16])[CH2:17][C:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)=[O:9])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 13004Cyclopropyl methyl ketoneHCID 69188Ethyl NicotinateHCID 10942334Sodium Methoxide

Product 1

HCID 123605591-Cyclopropyl-3-(pyridin-3-yl)propane-1,3-dione

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 39 g. of ethyl nicotinate, 33 g. of cyclopropylmethyl ketone and 18 g. of sodium methoxide in 400 ml. of benzene is heated under reflux for 6 hours. The mixture is diluted with 400 ml. of water and the benzene phase is separated. The aqueous phase is made weakly acidic with dilute hydrochloric acid and extracted with chloroform. The chloroform solution is dried over magnesium sulfate and concentrated under reduced pressure to give a solid. This solid is recrystallized from hexane to give colorless crystals, melting point 69°-70°C.

Workup

  1. additionA mixture of 39 g
  2. temperatureunder reflux for 6 hours
  3. additionThe mixture is diluted with 400 ml
  4. customof water and the benzene phase is separated
  5. extractionextracted with chloroform
  6. dry with materialThe chloroform solution is dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a solid
  9. customThis solid is recrystallized from hexane
  10. customto give colorless crystals, melting point 69°-70°C.

Sources & evidence

ORD record
ord-944728d0bf6b4422a2eafd50a1add28d
Source dataset
uspto-grants-1976_05
Patent number
US03957805

Reaction notes

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