Diisobutylaluminum hydride → 2-(4-Phenylphenoxy)ethanol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of (Biphenyl-4-yloxy)-acetic acid ethyl ester (0.63 g, 2.46 mmol) in dry toluene (15 mL) at −78° C. was added DIBAL-H 1M in toluene (4.92 mL, 4.92 mmol). The solution was stirred at −78° C. for 1 hour, warmed to room temperature and quenched with mixture of a solution of sodium tartrate in water and ethyl acetate for 1 hour. The layers were separated and the aqueous phase further extracted with ethyl acetate. The combined organic layers were dried (MgSO4), concentrated under vacuum and the residue purified bu column chromatography (silica gel, hexanes/Ethyl acetate 4:1, Rf0.1), 48%. 1H-NMR (CDCl3, 200.15 MHz): 7.58–7.26 (m, 8H); 7.00 (d, 2H, J=8.6), 4.14 (t, 2H, J=4.6), 4.02–3.98 (m, 2H); 2.04 (t, 1H, J=5.4).

Herkunft & Nachweise