2-Acetylpyridine → 2-Hydroxy-4-oxo-4-pyridin-2-ylbutyric acid ethyl ester

HRID 499149

Reaction equation

[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[O:3].[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)(=[O:10])[CH3:9]>C1(C)C=CC=CC=1>[CH2:6]([O:5][C:1](=[O:4])[CH:2]([OH:3])[CH2:9][C:8](=[O:10])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH3:7]

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of ethyl glyoxalate (3.060 g, 30.000 mmol) (6.2 mL of a 50% solution in toluene) and 2-acetylpyridine (3.630 g, 30.000 mmol) was heated in an oil bath at 135° C. for 16 hours. The crude residue after removal of toluene was purified by column chromatography. The pure 2-hydroxy-4-oxo-4-pyridin-2-ylbutyric acid ethyl ester was isolated in 44% yield (2.910 g, 13.000 mmol).

Workup

customThe crude residue after removal of toluene
customwas purified by column chromatography

Sources & evidence

ORD record: ord-cb01fbafd5a64462b5daf05bb07ec02c
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767677B2

Linked notes

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