Réaction #531871

Équation de réaction

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

Solvants

THF

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source