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, further after 10 minutes, 4-(chloromethyl)pyridine hydrochloride (5.00 g, 30.5 mmol) was added thereto little by little over three minutes under a nitrogen stream, 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, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ethyl 2-acetyl-3-(4-pyridyl)propionate (1.34 g, 18%) 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. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography

ORDレコード

ord-ae47110f0453402b8b529b5dee76f9ed

出典データセット

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07741346B2