Tetrahydrofuran → HCID 10719578, compound

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)

1. customTo a dry 15 ml 2-necked flask fitted with a serum stopper and a reflux condenser under argon
2. customto consume excess LiBH4
3. stirringthe resulting mixture stirred at RT under argon
4. waitAfter approximately 20 min
5. additionadded (20 ml)
6. customthe resulting layers partitioned
7. customseparated
8. washThe organic layer was washed with saturated NaCl (25 ml)
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. customevaporated
12. customto give a pale amber oil
13. washeluted with EtOAc/hexanes (3:7)
14. additionFractions containing product
15. customevaporated

ORD record

ord-36909f25b6d641e4a8b065580a6b75b3

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06169104A