Reaktion #157708

Reaktionsgleichung

4-tert-Butylphenylboronic acid

tri(2-furyl)phosphine

cesium carbonate

(2Z)-3-(5-chloro-6-methoxypyridin-2-yl)-3-iodoprop-2-en-1-ol

→

title compound

Ausbeute 101.6%

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

Ausbeute 101.6%

Lösungsmittel

ethyl acetate

1,4-dioxane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe reaction solution was left
2. 2
   Temperaturto cool
3. 3
   Filtrationfiltered
4. 4
   WaschenThe filtrate was washed with brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   FiltrationAfter filtration
7. 7
   Sonstigethe solvent was evaporated under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→1:1)

Vorschrift

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%).

Quelle