Reaktion #634073

Reaktionsgleichung

(4-Chloro-2-fluoro-phenyl)acetic acid methyl ester

(4-chloro-2-fluoro-phenyl)-acetic Acid Methyl Ester

2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl

potassium phosphate

4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl-2-methyl-phenyl)-1-penten-3-ol

(E)-3-ethyl-1-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1-penten-3-ol

sodium bicarbonate

→

title compound

Ausbeute 47.0%

Methyl (4′-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-3-fluoro-2′-methyl-biphenyl-4-yl)-acetate

Ausbeute 47.0%

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous layer was extracted with dichloromethane
2. 2
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe residue was purified by silica gel chromatography (17% ethyl acetate/hexane)

Vorschrift

(4-Chloro-2-fluoro-phenyl)acetic acid methyl ester (Example 40; 52 mg, 0.256 mmol), toluene (2.8 mL), palladium acetate (3.8 mg, 0.017 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (14 mg, 0.034 mmol), potassium phosphate (108 mg, 0.510 mmol) and water (0.28 mL) were added to (E)-3-ethyl-1-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl-2-methyl-phenyl)-1-penten-3-ol (Example 28; 83.6 mg, 0.170 mmol), and the mixture was stirred in a nitrogen atmosphere at 100° C. for one hour. The reaction solution was poured into a saturated aqueous sodium bicarbonate solution, and then the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (17% ethyl acetate/hexane) to give the title compound (42 mg, 47%).

Quelle