Ethyl Propionate → 1-(3-Pyridyl)propan-1-one

Temperature

100 °C

A mixture of ethyl nicotinate (15.1 g, 0.1 mole), ethyl propionate (15.3 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 pH 1 with concentrated hydrochloric acid (50 ml). The aqueous layer was heated at 90° C. for two hours, cooled, 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 ethyl 3-pyridyl ketone (b.pt 97°-99°/14 mm Hg).

1. temperatureAfter cooling
2. extractionextracted with diethyl ether (50 ml)
3. temperatureThe aqueous layer was heated at 90° C. for two 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

ORD record

ord-282a70bca2ca42218aea3b705d04acb7

Source dataset

uspto-grants-1994_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05352793