Tetrahydrofuran → HCID 10719578, compound

Participants

Reaction Steps

To a dry 15 ml 2-necked flask fitted with a serum stopper and a reflux condenser under argon was added methyl 3,5-diiodo-4-(4′-methoxyphenoxy)benzoate (1.02 g; 2.0 mmol) followed by 2M LiBH4 in THF (2.0 ml; 4.0 mmol). The mixture was stirred at RT overnight. EtOAc (10 ml) was added to consume excess LiBH4, and the resulting mixture stirred at RT under argon. After approximately 20 min, a moderate exotherm was observed and the reaction became cloudy. The reaction was digested with saturated NH4Cl (20 ml), EtOAc added (20 ml) and the resulting layers partitioned and separated. The organic layer was washed with saturated NaCl (25 ml), then dried over Na2SO4, filtered and evaporated to give a pale amber oil. The crude product was applied to a filter pad of silica gel (10 g, 230-400 mesh) and eluted with EtOAc/hexanes (3:7). Fractions containing product were combined and evaporated to give 592 mg (61%) of the product as a white solid. Crystallization from EtOAc/hexanes afforded 347 mg of 3,5-diiodo-4-(4′-methoxyphenoxy)benzyl alcohol (9) as a crystalline white solid. NMR (CDCl3) d 3.78 (s, 3H), 4.52 (s, 2H), 6.72 (m, 2H), 6.83 (m, 2H), 7.82 (s, 2H). TLC: Rf0.47 (EtOAc/hexanes, 3:7)

Provenance & Evidence