Reaktion #634091

Reaktionsgleichung

sodium hydroxide

(E)-(4′-{1-ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-2′,6′-dimethyl-biphenyl-4-yl)acetic acid methyl ester

ammonium chloride

→

compound

Ausbeute 84.0%

(E)-(4′-{1-ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-2′,6′-dimethyl-biphenyl-4-yl)-acetic Acid

Ausbeute 84.0%

Lösungsmittel

methanol tetrahydrofuran

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=1:1)

Vorschrift

A 1 N sodium hydroxide aqueous solution (0.181 mL, 0.181 mmol) was added to a solution of (E)-(4′-{1-ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-2′,6′-dimethyl-biphenyl-4-yl)acetic acid methyl ester (Example 58-(1); 31.8 mg, 0.060 mmol) in methanol-tetrahydrofuran (1:1, 4 mL), and the mixture was stirred at room temperature for 10 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride 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=1:1) to give the target compound as a colorless oil (25.8 mg, 84%).

Quelle