Ethyl butyrate → 1-(Pyridin-3-yl)butan-1-one

HRID 1707345Notes

Reaction equation

HRID 1707345 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:12](OCC)(=O)[CH2:13][CH2:14]C.[O-]CC.[Na+]>O>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1]([CH2:12][CH2:13][CH3:14])=[O:9])[CH:3]=1

Participants

5

Reactant 3

HCID 7762Ethyl butyrateHCID 69188Ethyl NicotinateHCID 2723922Sodium ethoxide

Product 1

HCID 4595021-(Pyridin-3-yl)butan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl nicotinate (15.1 g, 0.1 mole), ethyl butyrate (17.4 g, 0.15 mole) and sodium ethoxide (10.2 g, 0.15 mole) was stirred and heated under nitrogen at 100° C. for five hours. After cooling, the mixture was diluted with water (150 ml), extracted with diethyl ether (50 ml) and the aqueous layer made acidic to pH1 with concentrated hydrochloric acid (50 ml). The aqueous layer was heated at 90° C. for 2 hours, cooled, and made alkaline with solid potassium carbonate and extracted with diethyl ether (3×75 ml). The dried (magnesium sulphate) organic layer was concentrated and distilled to give propyl 3-pyridyl ketone (b.pt. 118°-120° C./14 mm Hg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether (50 ml)
  3. temperatureThe aqueous layer was heated at 90° C. for 2 hours
  4. temperaturecooled
  5. extractionextracted with diethyl ether (3×75 ml)
  6. dry with materialThe dried (magnesium sulphate) organic layer
  7. concentrationwas concentrated
  8. distillationdistilled

Sources & evidence

ORD record
ord-dab100e972c648f4912e857fa2bb0954
Source dataset
uspto-grants-1994_10
Patent number
US05352793

Reaction notes

Loading…