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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 70526Erstellt: 24. Oktober 2026

Cesium carbonate → (2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-ol

https://huagongshe.com/de/reaction/70526

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktCesium carbonateHCID 10796—
EduktTris(furan-2-yl)phosphaneHCID 521585—
Edukt4-tert-Butylphenylboronic acidHCID 2734320—
Edukt(2Z)-3-(5-Chloro-6-methoxypyridin-2-yl)-3-iodoprop-2-en-1-olHCID 58452855—
KatalysatorBis(dibenzylideneacetone)palladiumHCID 9811564—
LösungsmittelWaterHCID 962—
LösungsmittelEthyl AcetateHCID 8857—
Lösungsmittel1,4-DioxaneHCID 31275—
Produkt(2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-olHCID 58452849101,6%

Reaktionsbedingungen

Temperatur65 °C

Reaktionsschritte

4-tert-Butylphenylboronic acid (3.5 g), tris(dibenzylideneacetone)dipalladium(0) (183 mg), tri(2-furyl)phosphine (280 mg) and cesium carbonate (1.98 g) were added to a solution of (2Z)-3-(5-chloro-6-methoxypyridin-2-yl)-3-iodoprop-2-en-1-ol (881 mg) in 1,4-dioxane (20 mL)-water (10 mL) in a nitrogen atmosphere, and the mixture was stirred at an external temperature of 65° C. for 1.5 hours. The reaction solution was left to cool, diluted with ethyl acetate and filtered. The filtrate was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→1:1) to give the title compound as a light yellow powder (912 mg, 91%).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08822503B2
Quelldatensatzuspto-grants-2014_09
ORD IDord-08a57a96d9184121a1cb0aadff6dac11
Quellennotizuspto-grants-2014_09