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

HRID 359323

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

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

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

Sources & evidence

ORD record: ord-6ede371724bf47e7a016b39475c4275e
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05000946

Linked notes

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