Reaktion #531871

Reaktionsgleichung

trans-2-(4-Hydroxy-cyclohexyl)-isoindole-1,3-dione

triphenylphosphine

4-fluorophenol

diisopropyl azodicarboxylate

→

cis-2-[4-(4-Fluoro-phenoxy)-cyclohexyl]isoindole-1,3-dione

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated after 12 h
2. 2
   Sonstigethe resulting solid was purified by recrystallization from methanol

Vorschrift

To a solution of trans-2-(4-Hydroxy-cyclohexyl)-isoindole-1,3-dione 3 (1.0 g, 4.1 mmol), triphenylphosphine (1.3 g, 4.9 mmol), and 4-fluorophenol (0.55 g, 4.9 mmol) in 40 mL of THF was added dropwise at room temperature diisopropyl azodicarboxylate (0.99 g, 4.9 mmol). The reaction mixture was stirred overnight. The solvent was evaporated after 12 h, and the resulting solid was purified by recrystallization from methanol. Yield: 1.1 g (80% of theory). 1H NMR (300 MHz, CDCl3): δ 7.84-7.80 (m, 2H), 7.71-7.67 (m, 2H), 6.98-6.94 (m, 4H), 4.51 (s, 1H), 4.26-4.12 (m, 1H), 2.76-2.60 (m, 2H), 2.18 (d, J=13 Hz, 2H), 1.79-1.49 (m, 4H).

Quelle