Diisobutylaluminumhydride → HCID 11131640, compound

Participants

Reaction Steps

To a solution of 3,5-dichloro-4-(3-isopropyl-4-methoxy-phenoxy)-benzoic acid ethyl ester (prepared as described in Example 1, Step A) (100 mg, 0.26 mmol) in methylene chloride (3 mL) at −78° C. under nitrogen was added diisobutylaluminum hydride (1M in hexane, 0.6 ml, 0.6 mmol). The reaction mixture was warmed to room temperature and stirred for about 19 hours. The reaction was quenched with methanol (1 ml) and sodium potassium tartrate (0.5M aqueous solution, 2 ml). After stirring for about 15 minutes, the solution was extracted with methylene chloride (3×10 mL). The combined organic extracts were washed with saturated sodium bicarbonate and brine, dried, filtered, and concentrated. The crude product was purified by preparative TLC (methylene chloride) to afford the title compound (75 mg) as a solid. NMR (400 MHz, CDCl3) δ 7.39 (s, 2H), 6.85 (d, 1H), 6.69 (d, 1H), 6.43-6.46 (dd, 1H), 4.68 (s, 2H), 3.77 (s, 3H), 3.26-3.30 (sept, 1H), 2.03 (bs, 1H), 1.18 (d, 6H).

Provenance & Evidence