Potassium Phosphate, Tribasic → (4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-6-methoxy-biphenyl-3-yl)-acetic Acid Methyl Ester

Temperature

100 °C

(3-Bromo-4-methoxy-phenyl)-acetic acid methyl ester (Example 175-(1); 39 mg, 0.151 mmol), palladium acetate (2.2 mg, 0.010 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (8.2 mg, 0.020 mmol), potassium phosphate (64 mg, 0.303 mmol) and water (0.2 mL) were added to a solution of (E)-3-ethyl-1-(4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1-penten-3-ol (Example 39-(5); 48 mg, 0.101 mmol) in toluene (2 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for two hours. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to give the target compound as a colorless oil (26.2 mg, 49%).

1. extractionfollowed by extraction with dichloromethane
2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1)

ORD record

ord-9fb1d08e9cee4729aff018649e3e25f2

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935688B2