Reaktion #634092

Reaktionsgleichung

(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

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

potassium phosphate

(4-bromo-phenyl)acetic acid methyl ester

→

title compound

Ausbeute 93.1%

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

Ausbeute 93.1%

Lösungsmittel

toluene

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationAfter filtration through cotton plug
2. 2
   Einengenthe filtrate was concentrated under reduced pressure
3. 3
   SonstigeThe residue was purified by silica gel chromatography (17% ethyl acetate/hexane)

Vorschrift

A solution of palladium acetate (3.3 mg, 0.0146 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (12.0 mg, 0.0293 mmol) and potassium phosphate (62.3 mg, 0.29 mmol) in water (0.05 mL) and toluene (0.20 mL) was stirred for three minutes. A solution of (4-bromo-phenyl)acetic acid methyl ester (Tetrahedron Letters 44 (2003) 331-334; 36.0 mg, 0.15 mmol) and (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); 50.0 mg, 0.1049 mmol) in toluene (0.20 mL) was added, and the mixture was stirred in a nitrogen atmosphere at 100° C. for 1.5 hours. After filtration through cotton plug, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (17% ethyl acetate/hexane) to give the title compound (48.7 mg, 93%).

Quelle