Potassium Phosphate, Tribasic → (4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-biphenyl-2-yl)-acetic Acid Methyl Ester

Temperature

100 °C

(2-Bromo-phenyl)acetic acid methyl ester (Example 126-(1); 35 mg, 0.152 mmol), palladium acetate (2.2 mg, 0.010 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (8.2 mg, 0.016 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); 48.3 mg, 0.101 mmol) in toluene (3 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 (26.6 mg, 53%).

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-e38cb63d40224d6682e20bf5a7f17698

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935688B2