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

HRID 1076687Notes

Reaction equation

HRID 1076687 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-1f9e8f92c7784f0e9c65c60e06658bd9
Source dataset
uspto-grants-1976_05
Patent number
US03957805

Reaction notes

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