Diisopropylamine → Ethyl (Z)-3-(3,4-dimethoxyphenyl)-2-(3-pyridyl)-2-propenoate

Temperature

0 °C

n-Butyllithium (1.6M hexane solution, 99.2 ml) was dropped into a solution of diisopropylamine (23.4 ml, 166.6 mmol) in tetrahydrofuran (320 ml). The obtained mixture was stirred at 0° C. for 30 minutes. A solution of ethyl 3-pyridylacetate (24.0 ml, 158.9 mmol) in tetrahydrofuran (20 ml) was dropped into the resulting mixture at -70° C. and the obtained mixture was stirred at 0° C. for 15 minutes. A solution of 3,4-dimethoxybenzaldehyde (27.6 g, 166.0 mmol) in tetrahydrofuran (100 ml) was dropped into the mixture at 0° C. The obtained mixture was stirred at room temperature overnight, followed by the addition of water. The obtained mixture was extracted with ether. The organic layer was washed with water and a saturated aqueous solution of common salt, dried over magnesium sulfate and concentrated. The oily residue was purified by flash column chromatography (ethyl acetate/hexane=3:2) to give the title compound as a pale yellow oil (18.19 g, yield: 37%).

1. stirringthe obtained mixture was stirred at 0° C. for 15 minutes
2. stirringThe obtained mixture was stirred at room temperature overnight
3. extractionThe obtained mixture was extracted with ether
4. washThe organic layer was washed with water
5. dry with materiala saturated aqueous solution of common salt, dried over magnesium sulfate
6. concentrationconcentrated
7. customThe oily residue was purified by flash column chromatography (ethyl acetate/hexane=3:2)

ORD record

ord-b306a320788f41a5b4c77440dbb3afa3

Source dataset

uspto-grants-1996_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05530118