Water → HCID 22261866, compound

To a solution of 6-chloro-2-pyridinecarboxylic acid (10 g, 63.5 mmol) in tetrahydrofuran (150 ml) was added 1,1′-carbonylbis-1H-imidazole (11.3 g, 69.8 mmol), and the mixture was heated under reflux for 30 min. The reaction solution was cooled, and monoethyl malonate magnesium salt (10 g, 34.9 mmol) was added. The mixture was stirred at room temperature for 30 min. To the reaction solution was added water (200 ml) and the mixture was extracted with ethyl acetate (200 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl-acetate=4:1) to give ethyl 3-(6-chloro-2-pyridyl)-3-oxopropionate (7.96 g, 55%) as a brown oil. IR ν maxKBrcm−1: 1738, 1713, 1651, 1645. Anal. Calcd for C10H10NO3Cl: C, 52.76; H, 4.43; N, 6.15. Found: C, 52.63; H, 4.55; N, 6.02. 1H-NMR (CDCl3)δ: 1.20-1.40 (3H, m), 4.15 (2H×2/3, s), 4.14-4.32 (2H, m), 6.35 (1H×1/3, s), 7.37 (1H×1/3, d, J=6.6 Hz), 7.53 (1H×2/3, d, J=7.0 Hz), 7.70-8.02 (2H, m), 12.31 (1H×1/3, s).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 30 min
3. temperatureThe reaction solution was cooled
4. extractionthe mixture was extracted with ethyl acetate (200 ml×2)
5. washThe extract was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customevaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane:ethyl-acetate=4:1)

ORD record

ord-7b330baba9cf4114a8bdea02f6c7bbf9

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2