Reaktion #634074

Reaktionsgleichung

ammonium chloride

Methanol

sodium hydroxide

methyl (4′-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-3-fluoro-2′-methyl-biphenyl-4-yl)acetate

→

title compound

Ausbeute 78.0%

Sodium (4′-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-3-fluoro-2′-methyl-biphenyl-4-yl)-acetate

Ausbeute 78.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous layer was extracted with dichloromethane
2. 2
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe residue was purified by preparative TLC (chloroform/methanol=10/1)
5. 5
   workup.ADDITIONThe purified product was diluted with methanol
6. 6
   workup.ADDITIONAfter addition of sodium methoxide
7. 7
   Sonstigethe mixture was dried under reduced pressure

Vorschrift

Methanol (1.3 mL), tetrahydrofuran (1.3 mL) and a 1 M sodium hydroxide aqueous solution (0.133 mL, 0.133 mmol) were added to methyl (4′-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-3-fluoro-2′-methyl-biphenyl-4-yl)acetate (23.5 mg, 0.044 mmol), and the mixture was stirred at room temperature for 18 hours. The reaction solution was poured into a saturated aqueous ammonium chloride solution, and then the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (chloroform/methanol=10/1). The purified product was diluted with methanol. After addition of sodium methoxide, the mixture was dried under reduced pressure to give the title compound (17.7 mg, 78%).

Quelle