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

HRID 1973351Notes

Reaction equation

HRID 1973351 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 refluxed 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 refluxed 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-f5a0c95ce2fb488397178b51add1d39d
Source dataset
uspto-grants-1976_12
Patent number
US03997530

Reaction notes

Loading…