Tert-butyl acetoacetate → Ethyl 2-(4-pyridylmethyl)acetoacetate

Anhydrous N,N-dimethylformamide (41 ml) was added to sodium hydride (2.81 g, 70.3 mmol) under a nitrogen atmosphere, and the mixture was stirred under ice-cold water-cooling. A solution of t-butyl acetoacetate (6.33 g, 40.0 mmol) in N,N-dimethylformamide (20 ml) was added dropwise to the mixture over 10 minutes, after 10 minutes, 4-(chloromethyl)pyridine hydrochloride (5.00 g, 30.5 mmol) was added thereto little by little under a nitrogen stream over three minutes, and the temperature was raised to room temperature. After two hours, a saturated aqueous sodium hydrogencarbonate solution (150 ml) was added to the reaction mixture, and the whole was extracted with ethyl acetate (100 ml). The organic layer was washed with water (100 ml) and saturated brine (50 ml) successively and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give 1.34 g (18%) of ethyl 2-acetyl-3-(4-pyridyl)propionate as a pale yellow oily matter.

1. temperaturecooling
2. waitAfter two hours
3. extractionthe whole was extracted with ethyl acetate (100 ml)
4. washThe organic layer was washed with water (100 ml) and saturated brine (50 ml) successively
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationThe organic layer was concentrated under reduced pressure
7. customthe residue was purified by silica gel column chromatography

ORD record

ord-df3482e526fd41a5bb74b930ff3f7cda

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07098226B2