Cyclopropyl methyl ketone → 1-Cyclopropyl-3-(pyridin-2-yl)propane-1,3-dione

HRID 1973352Notes

Reaction equation

HRID 1973352 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([O:9]CC)=O.[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:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:9])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 13004Cyclopropyl methyl ketoneHCID 17307Ethyl 2-pyridinecarboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 123605601-Cyclopropyl-3-(pyridin-2-yl)propane-1,3-dione

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred mixture of 24 g. of ethyl picolinate, 18 g. of cyclopropylmethyl ketone and 11 g. of sodium methoxide in 250 ml. of benzene is heated under reflux for 6 hours. The mixture is diluted with 200 ml. of water and the water phase is removed. The aqueous solution is made weakly acidic with dilute hydrochloric acid. A solid precipitates and is collected by filtration. Recrystallization from cyclohexane provided colorless crystals, melting point 77°-78° C.

Workup

  1. additionA stirred mixture of 24 g
  2. temperatureunder reflux for 6 hours
  3. additionThe mixture is diluted with 200 ml
  4. customof water and the water phase is removed
  5. customA solid precipitates
  6. filtrationis collected by filtration
  7. customRecrystallization from cyclohexane provided colorless crystals, melting point 77°-78° C.

Sources & evidence

ORD record
ord-6b57eba596b842a893aacffcafb83516
Source dataset
uspto-grants-1976_12
Patent number
US03997530

Reaction notes

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