HCID 19374862, compound → Cyclopropyl(3-pyridinyl)methanone

HRID 128687Notes

Reaction equation

HRID 128687 reaction equation
[CH:1]1([CH:4]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[OH:5])[CH2:3][CH2:2]1>O1CCOCC1.[O-2].[O-2].[Mn+4]>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:4]([CH:1]2[CH2:2][CH2:3]2)=[O:5])[CH:7]=1

Participants

4

Reactant 1

HCID 19374862HCID 19374862, compound

Product 1

HCID 571581Cyclopropyl(3-pyridinyl)methanoneYield 80%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Dissolve 3.35 g of cyclopropyl(3-pyridyl)methanol, the compound obtained in the preceding step, in 75 ml of dioxane and add 13.66 g of manganese dioxide. After 4 hours of stirring under reflux, filter the reaction medium while hot through Celite. The organic solution yields, after evaporating under vacuum, a residue which is purified by chromatography on a silica column, using a mixture of cyclohexane and ethyl acetate (1:1 V/V) as eluent, to obtain cyclopropyl 3-pyridyl ketone.

Workup

  1. temperatureunder reflux
  2. filtrationfilter the reaction medium while hot through Celite
  3. customThe organic solution yields
  4. customafter evaporating under vacuum
  5. customa residue which is purified by chromatography on a silica column
  6. additiona mixture of cyclohexane and ethyl acetate (1:1 V/V) as eluent

Sources & evidence

ORD record
ord-4fc6f9c5d1b0483181f460d4592e1437
Source dataset
uspto-grants-1995_11
Patent number
US05464847

Reaction notes

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