Diethyl Ether → 1-(Pyridin-3-yl)heptan-1-one

HRID 484022Notes

Reaction equation

HRID 484022 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:8][CH2:9][CH2:10][CH2:11][CH2:12]C.C([Li])CCC.[Cl-].[NH4+].CC[O:23][CH2:24][CH3:25]>>[C:24]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)(=[O:23])[CH2:25][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 122863-BromopyridineHCID 25517Ammonium ChlorideHCID 178418244HCID 178418244, compound

Product 1

HCID 2227091-(Pyridin-3-yl)heptan-1-oneYield 36%

Procedure

A solution of 10.0 g (63.3 mmol) of 3-bromopyridine in 100 ml of ether was cooled to -78° C., to which 40 ml of 1.6M (64 mmol) n-butyllithium hexane solution was added dropwise. The mixture was stirred for 15 minutes after completion of the addition, to which a solution of 7.52 g (67.7 mmol) of heptanitrile in 15 ml of ether was added dropwise and stirred at -78° C. to room temperature further for 1 hour. To the reaction mixture an aqueous solution of ammonium chloride was added, from which the product was extracted with ethyl acetate. The extract was washed with water and dried, and the solvent was evaporated off. The residue was purified with silica gel column chromatography (eluted with isopropyl ether), to give 3.9 g (36%) of 3-heptanoylpyridine (an oil).

Workup

  1. additionwas added dropwise
  2. additionafter completion of the addition
  3. stirringstirred at -78° C. to room temperature further for 1 hour
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. customthe solvent was evaporated off
  8. customThe residue was purified with silica gel column chromatography (eluted with isopropyl ether)

Sources & evidence

ORD record
ord-53757950b9534f02a055386ca2ef643f
Source dataset
uspto-grants-1993_07
Patent number
US05229385

Reaction notes

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