Reaktion #634084

Reaktionsgleichung

(4-Bromo-phenyl)acetic acid methyl ester

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

potassium phosphate

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

sodium bicarbonate

→

compound

Ausbeute 29.4%

(E)-[4′-(1-ethyl-1-{4-[2-(1-hydroxy-cyclopentyl)-vinyl]-3-methyl-phenyl}-propyl)-2′-methyl-biphenyl-4-yl]-acetic Acid Methyl Ester

Ausbeute 29.4%

Lösungsmittel

toluene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionfollowed by extraction with dichloromethane
2. 2
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Vorschrift

(4-Bromo-phenyl)acetic acid methyl ester (Tetrahedron Letters 44 (2003) 331-334; 35 mg, 0.153 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 (65 mg, 0.306 mmol) and water (0.2 mL) were added to a solution of (E)-1-[2-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-vinyl]-cyclopentanol (Example 33-(3); 50 mg, 0.102 mmol) in toluene (2 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for 2.5 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=4:1) to give the target compound as a colorless oil (15.3 mg, 29%).

Quelle