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ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-ethoxyacrylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
94%
With bis(tri-t-butylphosphine)palladium(0); N-Methyldicyclohexylamine; lithium chloride; In 1,4-dioxane; at 110℃; for 20h;Inert atmosphere;
Preparation 7 (Z,E)-Ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-ethoxyacrylate Bis(tri-t-butylphosphine)palladium (47 mg, 0.092 mmol)) and lithium chloride (292 mg, 0.27 mmol) were added to a flask equipped with reflux condenser, and the apparatus was evacuated under vacuum and refilled with N2 several times. To this flask was added via cannula a degassed solution of anhydrous 1,4-dioxane (8 mL) under N2, followed by 3-bromo-2,6-dimethoxypyridine (500 mg, 2.29 mmol), N,N-dicyclohexylmethylamine (540 uL, 2.52 mmol) and <strong>[1001-26-9]ethyl 3-ethoxyacrylate</strong> (1.0 mL, 6.88 mmol), and the resulting orange solution was heated to 110° C. After 20 hours, the reaction mixture was cooled to room temperature, quenched with water and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 0-50percent EtOAc/heptane to yield the title compound (604 mg, 94percent) as an amber oil. 1H NMR showed the product to be composed of a 2.5:1 mixture of E/Z isomers.
93%
With bis(tri-t-butylphosphine)palladium(0); dicyclohexylmethylamine; lithium chloride; In 1,4-dioxane; at 110℃; for 16h;Inert atmosphere;
General procedure: A flask containing LiCl (980 mg,23.1 mmol), 2-bromo-4-fluoroanisole (1.0 mL, 7.7 mmol), DCMA (1.8 mL,8.4 mmol) and <strong>[1001-26-9]ethyl 3-ethoxyacrylate</strong> (3.3 mL, 23 mmol) in 1,4-dioxane(20 mL) was degassed by passing a stream of nitrogen through the mixturefor 10 min. Bis(tri-t-butylphosphine) palladium(0) (166 mg, 0.32 mmol) wasadded, and reaction mixture was heated at reflux under nitrogen for 16 h. Thebrown mixture was then cooled and partitioned between ethyl acetate andwater. The layers were separated, and the organic layer was washedsequentially with aqueous NH4Cl and brine, followed by drying over Na2SO4.The mixture was filtered, and the filtrate was concentrated under reducedpressure to give an oil which was purified by flash chromatography on silica(40 g, 10?50percent ethyl acetate in heptane) to afford 22c as an orange oil (1.93 g,92percent) as an inseparable mixture of E- and Z-isomers: 1H NMR (CDCl3, 500 MHz)alkene protons d: 5.21, 5.33 ppm (1:1 ratio); LCMS (ES): 269.2 (MH). HRMSCalcd for C14H17FO: 269.1184. Found: 269.1196.
Chemistry
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Material Science
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120K+ Compounds
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